


Rules and Regulations

by Anonymous



Category: Marvel, Marvel Cinematic Universe, Spider-Man - All Media Types, Spider-Man: Homecoming (2017)
Genre: Age Difference, Alternate Universe, Blackmail, Bondage and Discipline, Caning, Cock Cages, Cock Rings, Collars, Cruelty, Crying, Desperation, Detention, Emotional/Psychological Abuse, Face-Fucking, Figging, First Time, Humiliation, Jealousy, Leashes, M/M, Manipulation, Multiple Orgasms, Non-Consensual Blow Jobs, Non-Consensual Spanking, Obsessive Behavior, Orgasm Delay/Denial, Overstimulation, Private School, Rimming, Rough Sex, Sadism, Sexual Abuse, Snowballing, Threesome - M/M/M, Threesomes, Vibrators, Whipping, bastinado
Language: English
Status: Completed
Published: 2019-03-21
Updated: 2019-03-23
Packaged: 2019-11-26 20:51:21
Rating: Explicit
Warnings: Graphic Depictions Of Violence, Rape/Non-Con, Underage
Chapters: 4
Words: 23,164
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18185582
Author URL: https://archiveofourown.org/
Summary: “Headmaster, there’s a student here to see you. Professor Quill sent him to you for causing a disruption during gym class.”“Thank you Elise. Who is the student?”“Peter Parker, sir.”I paused. Peter Parker had been rather high on my list of students of ‘interest’ since I had been hired to replace the previous headmaster during the boy’s sophomore year, and as I’d watched him grow into his features, watched his lithe, athletic body fill out, he had begun to feature rather prominently in my daydreams. Alas, he was a model student and never had occasion to be sent to me for disciplinary action. I had assumed he would be, as many others had been over the course of my storied career, forever out of my grasp.Until now.My entire body thrummed with anticipatory lust. I could send Elise away and have him here and now if I chose, and it would be wonderful—perfect—his flawless, round ass red and sore from my spanking as I pressed him onto the cool surface of my desk, as I took him……but If I wanted Mr. Parker truly ensnared in my web, mine to do with as I pleased until his graduation, I would have to play this perfectly.





	1. Chapter 1

**Author's Note:**

> Some context before diving into this hellscape of a fanfiction, this is an AU where the Avengers aren't a thing, superheroes aren't a thing and none of the events of the MCU have happened. Peter attends Midtown Preparatory School for Boys, a fancy boarding school a la Dead Poets Society. You wont need any more information than that. Just know it's a rich school and Peter has no powers. While there are mentions of other MCU characters in this story, they really are merely references, and none of those characters ever make an appearance in this story. Peter is 17 in this fic, and the Headmaster is in his late 40s. It's a very dark fic, the Headmaster is *not* a very nice man. Do not take any of this lightly, it is not a happy story. The version of Peter in this fic is Tom Holland's Peter, though you can read it as any version of Peter you like (he is also a little bit more outwardly resilient than TH's Peter). I hope you enjoy, the whole fic is complete so I'll upload throughout the weekend.

Late one afternoon in October, as I was in the process of placing yet another in a series of tedious alumni fundraising calls, my secretary rang from the outer office.   
  
“Headmaster, there’s a student here to see you. Professor Quill sent him to you for causing a disruption during gym class.”   
  
“Thank you Elise. Who is the student?”   
  
“Peter Parker, sir.”   
  
I paused. Peter Parker had been rather high on my list of students of ‘interest’ since I had been hired to replace the previous headmaster during the boy’s sophomore year, and as I’d watched him grow into his features, watched his lithe, athletic body fill out, he had begun to feature rather prominently in my daydreams. Alas, he was a model student and never had occasion to be sent to me for disciplinary action. I had assumed he would be, as many others had been over the course of my storied career, forever out of my grasp.   
  
Until now.    
  
My entire body thrummed with anticipatory lust. I could send Elise away and have him here and now if I chose, and it would be wonderful—perfect—his flawless, round ass red and sore from my spanking as I pressed him onto the cool surface of my desk, as I took him…   
  
…but If I wanted Mr. Parker truly ensnared in my web, mine to do with as I pleased until his graduation, I would have to play this perfectly.   
  
“Send him in,” I said, affecting to sound bored as I pulled up his file.   
  
The door opened and he peeked his head around, wide eyed and nervous, before taking a seat in one of the sturdy wooden chairs in front of my mahogany desk. His delicate hands were folded together anxiously on his lap as he waited, while I feigned indifference to his presence and flipped through his file.   
  
The silence stretched out for several moments until he could stand it no longer and finally spoke. “I’m so sorry, Headmaster, I don’t know why I yelled at Professor Quill, or well, I do know, but I realize I was wrong and disrespectful and it won’t happen again—”   
  
I held up a hand and he ceased his babbled protestations immediately. I couldn’t really fault the boy, for whom amongst the students and staff hadn’t wanted to shout at Professor Quill at one time or another? But Peter certainly didn’t need to know that.   
  
“Do you know what the corrective penalty is for treating instructors in such a disrespectful manner?” I asked, finally looking up from my readings and meeting his beautiful, worried brown eyes.   
  
“Detention?” he whispered hopefully.   
  
“Yes. One week, here with me.”   
  
He nodded, looking grateful.   
  
“As well as 20 strikes with a wooden paddle for each day of your detention.”   
  
“Headmaster—”   
  
“I can make it 25.”   
  
His mouth snapped shut.   
  
“Luckily for you I’m free this afternoon. We can begin your punishment today.”   
  
He didn’t look as though that was particularly welcome news.    
  
“Attend to your homework, Mr. Parker. We’ll take care of the corporal aspect of your punishment at the end of the hour.”   
  
I could see his mind working to figure out if this was better or worse—an hour on a hard wooden chair after a paddling? Or an hour of anticipating the pain and humiliation to come?   
  
To be honest, I wasn’t sure myself. Both scenarios caused the boys in my charge to squirm deliciously in their seats; both scenarios required that I had strict control of my libido so they didn’t catch on too early in the game.   
  
He glanced at the wall to my left, where a series of ominous wooden paddles hung on the wall, an intimidation tactic that might have worked rather too well.    
  
Frankly, Midtown boys were extremely well behaved, to my detriment. I make no secret of my support of a good sound spanking to keep the boys in line. The parents know this when they entrust their children to me, and the students are given a detailed handbook of expected behaviors and punishments.   
  
Nobody is surprised, at any rate, when a student shows up to class with a face red with shame and a sore bottom. And nobody suspects a thing.   
  
Nobody except my most ‘special’ students, as Peter Parker was about to find out.

He pretended to work on his French homework while I made my alumni calls, though I could tell he wasn’t really concentrating on verb conjugation. His eyes darted constantly between his book and me, or the clock, or, most often, the wooden implements hanging on the wall. As I finished one of my calls by showering an embarrassment of praise on one of our top donors, I met his gaze and he dropped his eyes back to his book immediately.   
  
His anxious waiting was exquisite to behold. The cardinal blue blazer Midtown boys wore flattered his pale skin and chestnut hair admirably, but it was his expressive eyes and quirky mouth that constantly and consistently drew my gaze. I could not help but wonder how much more beautiful those eyes would be as they welled with tears while I administered his spanking; and that mouth, well, I could scarcely stand the anxious waiting myself, so eager was I to see those wide lips stretched, debauched, wrecked, after taking my cock.   
  
Though wait I would have to, for the moment. He was docile enough now, but I knew enough about Peter to anticipate some pushback if I tried to move too quickly or take too much all at once. He was often shoved around by the other boys, always supposedly ‘in jest,’ though of course I knew better, but he stood up for himself rather admirably considering his slight build. He had a tart tongue as well, and no compunctions about lashing out at those who picked on him or his friends. He was, in short, an impressively brave boy, and would have to be maneuvered into the position where I wanted him with extreme delicacy.   
  
I believed myself up to the task though, and so I set events in motion. I rose from my desk as twilight stole into my office, sweeping up my papers and arranging them in my briefcase. When the desk was clear, I met Peter’s frightened gaze again, and I beckoned him to me.   
  
“Come now, boy. It’s time for your punishment.”   
  
He walked on the trembling legs of a foal up to my desk as I turned my back on him to grasp one of the paddles from the wall.   
  
“Take your pants down, Mr. Parker,” I said, voice dripping with simulated boredom. “And your underthings as well.”   
  
I watched in the reflective glass of my window as he started at that, uncertain. It took him a great deal of time to wrestle with himself and finally follow my instructions, but that was to be expected.   
  
Midtown boys knew they could be spanked by the Headmaster at any time, but they were generally too embarrassed after the fact to compare notes. Was there a chance that he would confer with his fellow students, question whether everyone was administered a spanking on their bare bottoms? Of course. But the chance that he would actually ask Mr. Leeds or Mr. Osborn about the specifics of their own detentions after the fact were laughably miniscule. What teenaged boy would be willing to admit they’d been admonished like a toddler, after all?   
  
And so he pulled down his pants and, after another internal struggle, his underwear as well.   
  
And then I knew he was mine.   
  
“Across my desk, Mr. Parker.”   
  
He stretched his torso across the polished wood, arms extended over his head, and I had to pause and silently thank the Father for the gift I was about to receive.   
  
At the first crack of the oak paddle across his pale and trembling buttocks, he gasped.   
  
“That’s one,” I said, continuing my affected boredom at this whole proceeding. “I expect you to count from now on.”   
  
_ Crack. _   
  
“T-two,” he gasped.   
  
_ Crack. _   
  
“T-three, Sir.”   
  
His ass was every bit the teenage dream I’d imagined it would be. Perfectly round, pale globes that hid his most secret channel, and it took every bit of my willpower not to overpower and plunder him, drive my cock into that sweet ass again and again until I was sated... But I could be a patient man, and in the end, I knew it would be worth it.   
  
_ Crack. _   
  
_ Crack. _   
  
And again.    
  
And again.   
  
“Nine.”   
  
_ Crack. _   
  
“Ten, Sir, please stop,” he sobbed.

Well, he did ask. I laid the paddle aside for the moment and stepped up between his spread legs, cupped the blossoming warmth of his abused ass with my hands. At this turn of events, his frightened shaking stilled, and he looked over his shoulder at me with confusion and not a small amount of fear.   
  
“Eyes forward,” I commanded, and he obeyed.    
  
His buttocks were a fiery pink color and hot to the touch, and I longed to explore them further, but this was not the time. There would be other occasions to enjoy the perfection of Peter’s ass under my greedy hands, and so I resumed his punishment.   
  
_ CRACK! _   
  
“Eleven, sir!”   
  
And so it went, until he was crying out, “Tw-twenty, sir,” as tears poured down his lovely face.   
  
I have long been prideful about my impressive self control, but was I not a man? I could wait no longer, and stepped between his spread legs, allowing the wool of my trousers to roughly caress his abused thighs. I drew down my zipper and with one, two, three quick strokes, I spilled all over the precious dip of his lower back. He jerked in shock, looked over his shoulder at me, and then stilled again. In the polished glass of the window I could see his face awash in confusion and fear.   
  
I stood up and backed off, tucking myself away as he continued to look stunned at this turn of events.   
  
“Tomorrow, Mr. Parker. Promptly at 4 o’clock.”   
  
He rose from my desk, gave me a mistrustful look over his shoulder as he yanked his pants up over his flaming buttocks, and scurried from the room.   
  
When he was gone, and I was once again in control of my faculties, I reached for the phone and dialed the proper series of numbers. It was time to begin phase two.   
  
“Ms. Parker? It’s the Headmaster of Midtown. I’m afraid I’ve called to discuss your nephew's recent changes in behavior.”

* * *

 

The preemptive call I made to Peter's aunt had been terrifically helpful; May Parker turned out to be a concerned and conscientious parental figure, which had the potential to be my undoing, but I sensed as our conversation went on that she and her nephew shared a mutual protectiveness of one another, and that I could certainly leverage to my advantage.   
  
In any event, I could tell at a glance when Peter slunk into my office the next afternoon that his own call home had been greeted with firm but loving advice along the lines of keeping his nose to the grindstone and staying out of trouble.   
  
I greeted Peter on the second day of his detention with bland indifference and instructed him to brace himself; his paddling would take place first.   
  
The twenty strokes I administered swiftly and in a businesslike fashion, over his trousers, and when it was finished and he was pretending to read Moby Dick, I could see his mind working to understand what had just happened. He had clearly expected a repeat of the previous evening and as I observed him, I could tell he was beginning to doubt his interpretation of events, beginning to wonder if he'd mistaken my intentions--even though I had left him a memento in the form of my seed spilled along his back.   
  
The rest of the week followed the same pattern, and though I yearned to watch as his buttocks turned crimson during each spanking, I made do with my--rather vivid--imagination. By the time I released him on Friday, his punishment served, I'm sure he was convinced he'd imagined or misremembered our first night together. I've no doubt he believed he would stay out of trouble and never have occasion to be alone with me again.   
  
I, of course, knew differently.   
  
This would play out in one of two ways. Either he would be so disconcerted by our time together that he would begin to act out, contrary to his best intentions, and find himself once again at my mercy, or he would in fact do his best to stay well away from any situation that could lead to our crossing paths again. And if that were the case, well, I had a secret weapon.   
  
And so I waited, as October gave way to November, and conducted my business as usual, working for the betterment of Midtown Prep during the days and spending my evenings attending fundraisers or school events or the occasional dinner out with suitable women of my age. My status as a widower--something, it turned out, that I shared with Ms. Parker--afforded me some degree of protection from others finding out where my true predilections lay. One of these ladies had an attractive fifteen-year-old son, and it was a testament to my enchantment with Peter that I allowed our attachment to languish after only two dates.   
  
I was beginning to worry that it would require the assistance of that sleazy Professor Barton to entrap the beautiful boy when my patience was finally rewarded in the form of a schoolboy scuffle between my sweet Peter and the snot-nosed Flash Thompson.

They stood before me, Flash looking sullen and bored, Peter uneasy in the extreme.   
  
I shouldn't wonder, for it was obvious to me after only two minutes that Peter had suddenly found himself trapped in a room with two predators who had designs on him. As I informed them that they would both be enduring detention and a paddling, Peter flinched, his pale face turning positively white, while Flash...Flash's eyes darted down quickly to take in the swell of Peter's lovely round ass.   
  
A delicious morsel of information to file away for safekeeping, and I entertained a brief but exquisitely detailed reverie wherein I allowed Flash to observe Peter's bare-bottomed punishment, not for Flash's benefit but for my own delight at witnessing how the added humiliation of being on display in such a manner would affect Peter.   
  
(Of course, I had no intention of allowing a chump like Flash to impinge upon my time with Peter. But I knew Flash would be dealt with easily enough. He was clearly terrified of his true nature becoming public knowledge, and a suggestion during his detention that he leave Peter alone from now on lest ugly rumors begin circulating would do the trick.)   
  
Neither boy would tell me the nature of their argument, not that it mattered since I had deduced it for myself in a matter of moments. Still, I pretended to be a concerned educator, cajoling and entreating them for answers they would not give.   
  
Finally, when I'd grown tired of the charade, I pronounced their sentences.   
  
"Flash, twenty strokes with the paddle and one day of detention. You can serve it tomorrow before first bell."   
  
He looked quite shocked at this reprieve, as well he should, for he'd born several of my punishments already and knew I was no pushover.   
  
"Yes, sir," he said. "Thank you, sir."   
  
I turned to Peter. "Five days of detention, Peter. Each to be accompanied by 20 strokes."   
  
Peter blanched. "Sir," he began to protest.   
  
"That's 25."   
  
Flash almost looked as though he wanted to speak up on Peter's behalf, but I raised my hand to forestall him.   
  
"Flash, you're dismissed. I'll be awaiting your return in the morning."   
  
He looked from me to Peter and back again, uncertain, before his own sense of self-preservation won out, and he retreated.   
  
When we were alone again, I studied Peter in silence for several moments. He looked rather queasily at the ground in hopes that it might open up and swallow him whole. I smiled at him, not the reassuring smile I'd practiced in front of mirrors but a predatory smirk worthy of my true visage, that of a hunter circling his prey.   
  
"Peter, remove your clothing and bend over my desk."   
  
His looked at me then, pale eyes wide with shock, and I detected tremors in his deceptively broad shoulders as he shook his head. Then with a start he bolted for the door, rabbit-fast, but before he could wrench it open I said, "You're a scholarship student, are you not?"   
  
He froze but did not turn.   
  
"Sixty percent of your tuition is paid for by Midtown, if I'm not mistaken?"   
  
He turned then, back pressed against the door, and met my eyes.   
  
"Please, Headmaster," he began.   
  
I ignored him. There would be time later to catalog all the many ways I could make him beg, and undoubtedly give me many hours of pleasure during the cold New York winter.   
  
"Your aunt is so proud of you, Peter, for all that you've accomplished here. A delightful woman. It would break her heart if you were to be expelled, would it not? All the money she saved for your education amounting to nothing more than a diploma from a fourth-rate public institution?"   
  
His eyes blazed with the fury of righteous indignation, his body still prepared for flight.   
  
"To say nothing of your dreams of attending college at MIT next fall. Although I suppose the world could always use another fast food worker."   
  
He shook his head, still stubbornly refusing to accept that I had him right where I wanted him. Time to play my trump card.   
  
"And of course, for a woman who has already gone through so much, another broken heart might well be a death sentence."   
  
Ah, there it was. His entire body sagged, defeated, even as he continued to shake his head in mute refusal.   
  
I knew in that moment I had won.   
  
"Remove your clothes, Peter, and place them on the chair. I'll not ask again."

He was torn, I could see, his expressive features hiding nothing from me. He was calculating my sincerity, his aunt's constitution, and his ability to get out of Queens on his own with limited family resources and a stain upon his record. For a boy like Peter, escape from uptight attitudes offered the only possibility of future happiness, and yet he was no fool. I'd laid my cards upon the table, as the expression went, and he could no longer pretend that our first meeting was anything other than a gross abuse of power, which I intended to inflict on him again.   
  
His fingers strayed towards his belt buckle even as his feet remained rooted firmly to the ground. Finally, with a glare so full of loathing it was almost tangible, he crossed to my desk and pushed his pants and underwear to his knees.   
  
I was unmoved.   
  
"I said all your clothing, Peter."   
  
"No."   
  
"Then we're finished here."   
  
He studied me with uncertainty, one hand groping for his trousers.   
  
"You will return to your room and pack your things at once while you wait for your aunt to retrieve you."   
  
A soft note of misery escaped his lovely throat.   
  
"Please, Headmaster."   
  
"I only hope your aunt's heart is strong enough to withstand the news and circumstances of your expulsion."   
  
A perfect tear rolled down his face, causing my trousers to become uncomfortably tight. Still he refused to budge, frozen in an agony of indecision.   
  
"How well do you think she'll take the news that her sweet, kind nephew has been expelled for engaging in lewd behavior with another boy?"   
  
He looked shocked, but the flash of guilt that crossed his cherub features told me all I needed to know. That animal Flash had tried to engage with my Peter. He would be receiving a taste of my most fearsome paddle come the morning, the one with air holes added to minimize wind resistance.   
  
"But I didn't, he tried--" At the implacable expression on my face he broke off. His fingers finally began unknotting the tie around his neck.   
  
"Why are you doing this?" Peter asked, voice choking with anguish as he worked at the buttons on his white shirt.   
  
"Because I want to, Peter, and because I can."   
  
Slowly his layers were discarded, down to and including his footwear. His argyle socks had been darned repeatedly and expertly, I suspected by Peter himself. The sight enhanced both his fortitude and vulnerability in my eyes, and made me desire him all the more.   
  
With each article that was removed my cock grew harder, and this time I did not disguise it from him. Naked, he was every bit the vision I'd imagined he would be; pale, lean, and long-legged, with a taut belly and an unexpected layer of muscle usually hidden by his uniform. The perfect curve of his buttocks was a poem.   
  
I indicated that he was to stand at the foot of my desk with his legs spread wide.   
  
"Now lay across the surface, hands over your head."   
  
He struggled with the command, tears coursing down his face, but in the end he obeyed.

Each blow was accompanied by a loud cracking sound. Peter counted as directed, and did not start begging until the twentieth stroke. When it was over and his luscious ass resembled the hue of a ripe strawberry, I unbuttoned my trousers and once again stroked myself to completion, my seed spattering across his abused bottom and the dip of his back.   
  
How I longed to bury myself in his tight passage! But he was far from broken, and I feared that if I pushed now, he would disappear from my life forever; furthermore I knew I could never settle for just one night of carnal pleasure with my sweet boy. I intended to enjoy him time and again until he was finally and forever pulled from my grasp upon his graduation from Midtown Prep.   
  
When his spanking was finished he cried silently, body wracked with noiseless sobs, but after a few moments he began to pull himself together. He made as though to stand and retreat to the study desk in the corner, but I pressed him back down with a firm hand between his shoulder blades.   
  
"I did not tell you to move."   
  
He let out a soft moan but said nothing, and I struck him lightly across his flaming cheeks with a bare hand.   
  
He gasped, and then choked out quickly, "Yes, Sir!"   
  
I reclined in my oiled leather chair and gazed upon his delectably defenseless body for a time.   
  
"Do you not wonder, Peter," I said finally, breaking the silence of the room, "why your punishment was more severe than Flash's?"   
  
"Sir?" he sniffled.   
  
"It is because I know what a terrible tease you are. I see how you behave, how you flaunt yourself in gym shorts at least a size too small. It's little wonder that Flash could no longer control himself in your presence." As I spoke, I traced my name upon his back with the cooling streaks of my own ejaculate.   
  
"I'm sorry, Sir." His voice was muffled as he spoke into the polished surface of my desk.   
  
"No, not yet, but you will be."   
  
I picked up the phone then and began to dial, each long turn of the rotary sounding overly loud in the quiet of my office.   
  
"Hello, Ms. Parker?" I began, and Peter's entire body stiffened. "I'm afraid Peter's been involved in a bit of trouble again."   
  
We spoke at length about Peter, a good boy going through a rough patch, his aunt was quick to point out. I agreed, with gentle suggestions that a firm hand was required to help steer him on this last leg in his journey to adulthood.   
  
Peter endured this conversation stoically; naked, abused, and wearing the marks of my lust upon his body.    
  
Ms. Parker was a charming woman, and she had raised a good surrogate son. It was Peter's particular bad luck and nothing more that had steered him into my path. Were I in May Parker's shoes and knew the truth, I might rail against the heavens, whereas I myself was ecstatic to find that the Father was once again standing by my side.   
  
"Peter's a special boy," Ms. Parker hedged at one point in our discussion, and I murmured banal words of agreement. Any doubts I might have had about Ms. Parker's knowledge of Peter's true inclinations were extinguished by the end of our talk; she cared not a whit that society would deem Peter a deviant, an insight I would be sure never to share with the dear boy.   
  
May Parker, I was convinced, would in fact move heaven and earth to protect her boy. It was my charge to give her no cause to.   
  
Peter dressed at the end of the hour and fled to his dormitory, only to return the next night and the next to bear the same punishment. He would strip, lay upon my desk, and withstand both a bruising spanking and the humiliation of my release upon his body. He would remain in such a position, my release drying on his fair skin, until I waved him away at the end of each hour.    
  
His altercation with Flash had taken place on a Tuesday, and I was beside myself that weekend wondering if he would return on Monday evening. I was confident that throughout every step of our relationship thus far that I had played the correct hand, the winning hand, but even the best cards must bow to Lady Luck now and again.

But he did return to me that Monday for his final punishment, shooting me a cold look as he removed his clothing. He was still angry, still a fighter, but in one week he had grown complacent to the horrors of being naked in my presence, as we all succumb to ongoing horrors lest we go mad.   
  
So he laid across my desk once more--for the last time, I’m sure he assumed--toned arms stretched above his head, shoulders pressed to his ears, but on this night I grasped his thin wrists in my hands and tucked them tight against the small of his back before tying them together swiftly with his own blue-red striped school tie. He fought against this fresh humiliation, frantic and fierce, but still he held his tongue, making no further, futile effort to sway me.    
  
It would seem he had decided to get through this last official detention in silence and then be rid of me once and for all.   
  
He was only half correct; he would indeed be silent, but he would never be rid of me.   
  
While Peter twitched ineffectually against his new bindings, I scooped up his own underwear from the floor and stuffed them between his lips.   
  
He bucked and strained against this new indignity, frightened all over again by my capabilities and no doubt disgusted by the taste of his own cock. But it was too late. He was bound and spread and gagged; he was completely at my mercy.    
  
"Ahh, Peter, my sweet boy," I said, stroking my hands along his bruised bottom. "Now, your education shall truly begin."   
  
He jerked again at those words, and thrashed against his restraints even while I hammered away at his ass with my most wicked studded paddle.   
  
I counted for him as muted screams tore from his throat--20, 30, 40 strokes. At number 26 he looked over his shoulder and gave me such a baleful look that I might have been frightened if our roles were reversed.    
  
He was a stubborn boy, and tried to escape more than once, tried to wrench himself free and bolt for the door, consequences be damned, but his restraints assured that he had no leverage. He barely managed to bring his chest up off of my desk in his throes, and he was still rather small for his age, whereas I was quite fit for being 30 years his senior. It was nothing for me to press my weight against his back until he stopped fighting his fate.   
  
He was, in sum, no match for me, and I forced him to accept this fact as I spanked his bottom till my own brow was sweaty and Peter rested limply against my desk, beaten and finally bested.   
  
When his spanking was completed and Peter little more than a bound puddle of pain, I retreated to the corner of my office, poured myself three fingers of Scotch, and waited for him to settle.   
  
It was some time before his wretched sobs had finally quieted, but when they did I was ready, and eagerly stepped up behind him, the rough wool of my suit pants scratching at his tender flesh in a grotesque reenactment of our first night together.   
  
I slipped a greased finger into his ass, and it was the very definition of heaven.   
  
He jerked in his bonds again, thrashing wildly, but he had no traction, and it took no effort at all to add more fingers until I was sure he could take me without undue discomfort to my waiting cock.   
  
And take him I finally did! When at last I sank my swollen cock into his virgin hole, my hands squeezing fresh bruises on to his sweet, purpled cheeks, we both cried out, I in ecstasy and he in the utmost of agony.   
  
I drove into his slick, abused ass again and again, hungry for completion even as I tried to forestall my release, but I had desired Peter for far too long, and to my shame I was finished in a matter of minutes.   
  
When I was spent, and my semen was dribbling out of Peter’s ass, I unbound him and gathered him onto my lap. His sobbing would have been heartbreaking, had I a heart.   
  
"Shh," I soothed. "That's all done with, and now you're a man."   
  
His distress was almost enough to make me harden again, quite a feat for a man of my age. But the way his pale body shook, how he would simultaneously accept my caresses and shy from my touch, was the very definition of intoxicating.   
  
I was truly an addict.   
  
I had tasted, but I needed so much more.

When his tears had finally dried, he stirred in my arms.   
  
"Is it over?" He asked, his usually melodious voice quite rough from his earlier screaming.   
  
"Your punishment is over, yes," I said. I placed him on his feet, his legs wobbling, and went to retrieve an item from my sideboard. He flinched when I handed him the tube of ointment.   
  
"I don't think you were damaged tonight," I said, "but I want you to apply that for the next few nights just in case."   
  
He studied the tube doubtfully and I added, "Internally."   
  
His fingers spasmed but he maintained his grip on the tube.   
  
"I'll let you heal for a few days before we do that again."   
  
"Oh, thank you, Sir," he said, voice dripping with venom.   
  
"In the meantime I have other things to teach you. So many things... I expect you to be at my office every day at 4 unless you have choir practice."   
  
"You said it was over!"   
  
"I said your punishment was over. Tomorrow you begin your internship. It will look wonderful on your college applications. I know how keen you are to apply for a job with Stark once you graduate college."   
  
He shook his head but I ignored him. "Your aunt was so pleased when I called to inform her that I'm offering you this opportunity. The position comes with a small stipend to be put towards your tuition. She asked me to pass along her hearty congratulations."   
  
"Please, no." His eyes were welling again.   
  
"And lest you think you can deceive me, I've already secured a copy of your extracurricular schedule from Professor Lang." I cupped his charming face in my large hands. "That will be all for tonight."   
  
"Yes, Sir."   
  
He dressed slowly, flinching as he pulled his trousers up over his abused ass. He walked stiff-legged towards the door, pausing before he left to look over his shoulder.   
  
"You're a vile person."   
  
I smiled. "On that at least, we're in accord. Good night, Peter."


	2. Chapter 2

Unfortunately, between Peter's studies and my own duties, it was several days before I could get the boy alone again. The following afternoon, I was forced to entrust Elise to find some small tasks for Peter to complete before he began his studies so that I could attend to the discipline of a brutish student, who apparently had learned enough in his classes to curse out Professor Potts en français.   
  
To be forced to paddle this student when I was aching to have Peter naked and at my mercy again was not ideal; however, though I was not in the least attracted to his bulky body, I did so enjoy inflicting pain. I held back not a bit, since his tomfoolery had interrupted my plans for Peter.   
  
And so it was Friday afternoon before we found ourselves together again.   
  
"Have you enjoyed working with Elise this week?" I asked as I locked the office door and drew the blinds.   
  
"I've enjoyed not having your creepy paws all over me this week," Peter snapped.   
  
"An unfortunate situation I intend to rectify at once," I said. "Remove your clothing and place the items on the chair."   
  
He glared at me, but he was, as I've noted, an uncommonly bright boy, and he removed his garments without any futile protestations.   
  
I pressed him once again onto the surface of my desk, the better to inspect my previous handiwork. His bottom was a riot of colorful bruises; the broader strokes already yellowing with age while starbursts of purple from the studded paddle still littered his backside. I was pleased to note that I had broken no skin nor caused any permanent marks in my vigor. Within a few days time, his gorgeous ass would once again be a perfect blank canvas for me to decorate.   
  
"It must be quite uncomfortable to sit through your classes on our hard, wooden chairs," I remarked. He stayed silent, and I smacked his bruised left cheek in warning.   
  
"It is, Sir," he said through gritted teeth.   
  
I pried his cheeks apart to inspect his hole and though his entire body twitched at my trespass, he did not fight me. His lovely passage was a healthy pink color, and showed no signs of distress or damage from our brutal coupling.   
  
I blew gently on his hole, and he reared up at that, his legs kicking back at me though of course I dodged them easily.   
  
"Sensitive," I noted with approval as I backed away. "Stand, please."   
  
He rose up then, arms crossed defensively across his toned chest while he awaited further instruction.   
  
"Tell me, Peter, have you ever been kissed?"   
  
He shook his head.   
  
"No? Not even by one of the looser young ladies at Miss Romanoff's Finishing School?"   
  
He blushed at that. "Ahh, so you have kissed, then," I deduced. "Just not by anybody you desire."   
  
He nodded in agreement, abashed.   
  
"How does it feel then, Peter, to know that you'll have my cock between those lips before they touch any beau you might fancy?"   
  
He shook his head as tremors raced through his body. "Please, Sir, no!"   
  
I tsked. "I am teaching you all the ways there are to please a man, Peter. You should be thanking me."   
  
His eyes brightened with unshed tears, a sight I was sure I'd never grow tired of.   
  
"To your knees, Peter. Let the lesson begin."

He sank gracefully to the floor and knelt before me, his face a study in misery.   
  
"Undo my trousers and take out my cock."   
  
He remained motionless, undergoing some mental turmoil no doubt, and I smiled indulgently. "Poor boy, would it perhaps be easier if I bound you again?"   
  
"No Sir," he said quickly, reaching for my pants. He was wrong, of course, not yet understanding how his acts of 'compliance' would come to torture his thoughts over time. But that at least was a lesson he would have to learn on his own.   
  
"You may begin by using your hands along my shaft while you lick at the head. Pretend it is an ice cream cone you are enjoying on a warm summer’s day."   
  
He began timidly, just the barest brush of his hand along my cock accompanied by tiny darting licks. What he lacked in skill, he did not make up for with enthusiasm. Fortunately I was an excellent educator.   
  
"More of your tongue, use the flat of it; that's it. Gentle with your hands, and mind your teeth."   
  
He followed my orders well enough but still lacked zeal. I let his tentative ministrations continue for several minutes.   
  
"At this rate," I told him finally, threading my fingers through his soft hair, "you will still be at your task come midnight." He picked up his pace then, sucking on the sensitive head while his fingers flew along my shaft.   
  
"Use your tongue on the slit, there's a boy. Can you taste how much I desire you? Now take my balls into your mouth." He did so with no hesitation, following my instructions with mindless fervor in order that his ordeal should end sooner, but I was enjoying his warm, wet mouth far too much to finish prematurely this evening. I let him lave and suck on my cock and balls for the better part of an hour, until his lips were red as any starlets, though much prettier in my estimation, and his body was beginning to slump with exhaustion. Then I took matters into my own hands.   
  
"Give me your arms, Peter."   
  
He pulled off with a wet pop and stopped his labored stroking, reaching up as I crowded closer, trapping him between my body and the edge of my desk. With one hand I pinned his slender wrists over his head against the surface of the desk, while my other hand caressed his soft face.   
  
Then I began fucking his throat in earnest.   
  
His eyes flew open in panic, his head rocked back against the desk as he choked and gagged on my cock. My thrusts were deep enough that I experienced the delightful fluttering of his throat about my cock head. His hands sought to push me away, batting at me ineffectually as he struggled for breath, but I was much the stronger man, and held his wrists in a bruising grip. In the end he could do nothing but submit, taking great heaving gulps of air when I permitted, and coming perilously close to losing consciousness when I did not.   
  
Neither of us could have withstood this for terribly long, and too soon--for me, at any rate--I was instructing him to swallow. I emptied myself long and deep into his mouth, hips stuttering as the hot spurts of my ejaculate filled his throat.   
  
When I withdrew he collapsed onto his side, coughing and gasping, tears spilling down his face, every bit the debauched angel I’d been longing to see since our very first encounter.   
  
I tucked myself back into my trousers and then picked him up off the floor, settling into my chair and holding him in my lap once again. He struggled to get away but had not the strength to put up any serious fight, and in the end he was forced to curl up against me, sobbing, while I petted his hair and whispered soothing words of nonsense.   
  
"Don't fret, dear boy," I murmured when finally he had quieted. "In time you will come to find that practice does indeed make perfect."

* * *

I did not lay hands upon Peter the following week, choosing instead to direct him in pleasuring himself for my entertainment. I detected, from the hateful looks he shot me as he stroked and fingered himself to orgasm, that he would have quite preferred the paddle. He tried to look away from me in his shame as he writhed upon my desk, but I would have none of it.

"Eyes to me, Peter," I said when he tried to once again to hide his face with his unoccupied hand. "Now pinch your nipples. Harder. No, don't stop stroking."   
  
Watching him climax against his will was almost as breathtaking as forcing myself upon him. When I leaned over his prone form to sample his issue with my tongue, his mortification was complete.   
  
That Thursday, just before Midtown's Thanksgiving break, found me once again hosting the annual faculty dinner party before the instructors disbanded for the holiday. It was a necessary engagement that I usually greeted with dread, although this year I found the gossip quite enlightening.   
  
"Flash has been bothering Peter again, I'm sure of it," Professor Steve Rogers confided at one point. "Peter has the most terrible bruises on his arms, and won't say where he got them."   
  
"A shame," I murmured. "More wine?"   
  
He looked at me askance, no doubt still annoyed that I had punished Peter as well as--and more harshly than--Flash after their last altercation.   
  
"It is a shame. Peter's a good boy," Steve avowed. It was a testament to my iron will that I did not harden in my pants at the phrase.   
  
"Parker," snorted Professor Barnes. "Bit light in the loafers if you ask me. He's going to get that Leeds boy into trouble same as Thompson, mark my words."   
  
"Ned Leeds?" I asked innocently as my pulse began to race.   
  
"I've seen them canoodling in the study lounge," he affirmed. "Whispering together, and giggling. And poor Ned is such a sweet boy."   
  
"Indeed," I demurred. "Now tell me, who's ready for dessert?"   
  
The next day I took an impromptu stroll through the student cafeteria, where I saw with my own eyes how close Peter sat upon the bench seat next to Ned, how he threw his head back and laughed at some inanity the Leeds boy had just made.   
  
Of course, it was to my benefit that Peter appeared to be happy amongst his peers; I certainly did not need the bother of an inquiry about how withdrawn Peter had become, how he'd lost weight, etc.   
  
Still. This would not do at all.   
  
An ugly jealousy bloomed within me and I knew I could not bear for this flirtation to continue.   
  
Later that afternoon, as Peter lay upon my desk with two of his own fingers buried in his ass, I told him that I expected him to spend a portion of his vacation with me.    
  
He was, understandably, quite upset, as he'd assumed he'd be free of my presence for almost two weeks.   
  
"My aunt!" he protested.   
  
"Your aunt has been taking on more shifts than she can handle," I chided. "I imagine she will be relieved to have you taken off her hands for a few days. Now, insert another finger, I know you can take more."   
  
He blushed crimson but did as he was bade.   
  
"Your aunt will be working through next Thursday to share the afternoon with you," I continued, watching with no small amount of interest as his fingers worked at his hole. "So let's say you're mine from Thursday night until Sunday."   
  
"No," he hissed. "You can't have my weekends too!"   
  
"Can't I?" I asked, my voice dripping with disdain. "Now crook your finger a bit; there's a good boy, how does that feel?" I asked, noting that he must have grazed his prostate if the twitch of his cock was any indication. "And kindly remember that it is I who tells you what to do. Thursday at 5 o'clock at the Headmaster's House. And do be prompt."   
  
Alas, perhaps fortified by our days apart or his visit with his aunt, Peter did not show up at the appointed time. I stewed and paced about my study as 6 o'clock became 7 became 8.   
  
Finally, consumed by a white-hot fury, I could stand to wait no longer. I donned my overcoat and strode through the falling snow to Danvers Hall to confront Peter.

By the time I arrived at Peter’s dormitory, I had somewhat composed myself. I was still quite displeased that he had disobeyed me, but no longer nearly boiling over with anger.   
  
That is, until my knock upon his door was answered by none other than Ned Leeds! It took every ounce of willpower I had to maintain a pleasant facade.    
  
"Headmaster!" Ned exclaimed, eyes widening in surprise. "Is everything alright?”   
  
“Quite so, Ned, and happy Thanksgiving to you. Is Peter available? We had an appointment to review his college applications, but it must have slipped his mind.”   
  
“Yes, of course, come in.” Ned stepped back from the door and I entered to see Peter huddled on the leftmost bed, looking quite small and unhappy.   
  
“Peter wasn’t feeling well, so I stopped by to keep him company,” Ned said. “We were just listening to some music,” he added hesitantly. I glanced about the small room, where a smartphone was propped up on a desk, music playing quietly from its speakers.   
  
“Thank you, Ned. Would you please excuse us?”   
  
He glanced at his friend and then said, “Of course. Feel better Peter. Happy Thanksgiving, Headmaster.” He grabbed his coat and left.   
  
When we were alone, Peter drew into himself even further, arms wrapped around his legs in a defensive posture, watching silently while I walked about inspecting his things. DVD cases littered the floor, from sci-fi and fantasy to romance to horror. One side of the room, presumably his roommate’s, was decorated with football pennants while the other held posters for 80s cult classics. Except for the DVDs, it was uncommonly tidy for a small room that housed two teenage boys.   
  
“Where is your roommate tonight, Peter?”   
  
“Visiting his grandparents, Sir,” he said in a small voice.   
  
“Until Sunday?”   
  
“Yes, Sir.”    
  
“Would you care to explain why you chose to ignore my summons?”   
  
He straightened and glared at me. “I shouldn’t have to follow your stupid orders on weekends,” he snapped, regaining a little of his customary bite. "I shouldn't have to at all!"   
  
I sat next to him on the bed and placed a hand on one trembling thigh.   
  
“So you don't want to spend the next few days as my houseguest?"   
  
He shrugged, in that infuriatingly morose manner at which adolescents so excel.   
  
"Of course, I understand if you don't want to stay with me," I said. He eyed me with suspicion.   
  
"Perhaps instead, we could spend some time together here?” I slid my hand up his leg and then squeezed his cock through his trousers until he gasped. “Would you prefer that Peter?”   
  
He shook his head rapidly.   
  
“Would you like me to fuck you here, Peter?” I whispered into one delicate ear as I pressed him down onto the bed. “In your own bed? So you can remember our happy times together as you’re trying to fall asleep at night?"   
  
He shook his head, his eyes huge with alarm.   
  
"So you can smell my semen as you’re studying, after it has dribbled out of your ass? So you can remember the taste of my cock as you're talking with that imbecilic friend of yours?”   
  
“Please, no,” he whispered, beginning to cry.   
  
“Because if you won’t show up for our engagements, I will come to you Peter. I will fuck you in every corner of this pathetic little room, so you can never escape me in your thoughts.”   
  
"No, please no, I'm sorry," he cried, wiping his eyes.   
  
I released him and stood up, straightening my coat. “Then I suggest,” I said coldly, “that you accompany me to my quarters. Immediately.”   
  
He scrambled from the bed and hastened to put on his shoes.   
  
"Don't forget your schoolwork ."   
  
He stuffed his books and papers into his satchel, studiously avoiding my gaze.   
  
We walked in silence the five minutes it took to cross campus and reach my home, a Georgian brick that matched the rest of Midtown's buildings. As soon as we were across my threshold, the tiresome world locked out, I marched him upstairs to the master bedroom and ordered him to strip.

Once in my bed chamber, Peter slowly peeled out of his sweater, a lovely rich blue that flattered his coloring exceedingly, and then began fumbling with the buttons of his pants. As he undressed, his eyes never once strayed from the massive, iron worked four-poster bed that dominated the room. He moaned softly when he spotted the chains and manacles that hung from the top of each post.   
  
When he was finally divested of his comfort-over-style clothes, I steered him to the bed. He began to bend over it with an air of resignation but with a click of my tongue he straightened.   
  
"Eyes to me, Peter. We need to have a serious discussion about your behavior today, and how we are to proceed from here."   
  
He turned his back to the bed, holding up his arms when I indicated so that I could affix his wrists to the iron posts at each corner. When I was finished, I stepped back and drank in the sight of him. He was stunning, standing naked and vulnerable with his arms stretched out above his head, every inch of his creamy skin on display. His cock hung listlessly between his legs, surrounded by a fine thatch of soft brown curls. He saw my hungry glance and he blushed.   
  
"I hate being tied up," he muttered, wrists tugging nervously against his bonds.   
  
"And I hate being stood up for an appointment. What a disappointing day for us both."   
  
"Just do what you're going to do and get it over with!" he growled.   
  
"Silence!" I thundered, as finally I began to give voice to the anger that had been simmering within me for hours. "You will listen to what I have to say and you will not make a sound!"   
  
I went to the closet and returned carrying a thin wooden switch.   
  
"I thought you were a bright boy, Peter," I began. "I thought we'd reached an agreement that worked to our mutual benefit. I thought you understood that your obedience in this matter was to be absolute."   
  
"I'm sorry, Sir," he began, eyes transfixed on the slim length of wood. With a deft flick of my wrist, I landed a stinging blow to his right flank. He jolted against the restraints, hands clinging to the chains for balance.   
  
"I believe you were instructed to be silent."   
  
He nodded quickly.   
  
"I thought we'd reached an agreement," I repeated, "whereby you submit to me completely, in exchange for your continued presence at this school and the welfare of your family."   
  
He opened his mouth to protest, and I added a matching thin, red welt to his left flank.   
  
"As your bottom is currently out of my reach in this position, the next time I strike you it will be upon your cock. I suggest you think very hard about whether your protestations will be worth it."   
  
He clamped his mouth shut.   
  
"Since you seem to be somewhat confused about the terms of our arrangement, I will lay them out explicitly. If you defy me again, you will be immediately expelled from McKinley for engaging in lewd acts with another boy. Your family will be shamed and your future ruined."   
  
As I spoke I retrieved the corner chair from its spot and placed it in front of him so I was eye level with his cock.   
  
"In addition, I will notify the proper authorities about your transgressions. Are you not aware, Peter, that sodomy is illegal in this state, punishable by time in a correctional facility?"   
  
"Sod--I was a virgin before I met you!"   
  
The switch landed upon his cock and he howled in pain.   
  
"That is your last warning, Peter. Nod if you understand."   
  
He nodded vehemently, face suffused with pain.   
  
"You might think that sodomy is a crime not often prosecuted these days, and you would be correct. So distasteful to the unenlightened, and such. But I have many friends, Peter, friends with interests similar to mine. Judges. Attorneys. If I say the word, you will be prosecuted, and you will end up in prison, where I'm sure you'll find many of the tricks I've taught you will be quite useful. As it turns out, a number of men are willing to turn to sodomy if no other opportunities for release are available."

He looked utterly hopeless at this revelation, completely defeated, but I'd seen him look as such on earlier occasions, and so I pressed on.   
  
"With you locked away from me," I said quietly, as I began stroking his unwilling cock, "it is safe to assume that I will be quite lonely, quite in need of diversion."   
  
Anticipating my next words, he began shaking his head in mute horror.   
  
"Tell me, Peter, how do you think young Mr. Leeds would look impaled upon my cock? He's said to be quite an agreeable boy. So very eager to please others. Do you think he would please me?"   
  
I quickened the pace of my hand, and though he struggled internally, he finally succumbed, his cock swelling admirably in my grip.   
  
"You may speak now."   
  
"Please, no, please, I'll be better, I'll do everything you say, please please please..."   
  
"You will obey my every command until your graduation?"   
  
"Yes, I promise, don't send me away, don't hurt him..."   
  
"You will obey my every command with enthusiasm?"   
  
"Yes, yes, I promise!" He moaned brokenly as I continued to work at his shaft, cupping his sac with my unoccupied hand. "But what about next...next year?" he added breathlessly, as I thumbed at his wet slit.   
  
"If you please me in all ways, Peter, I will never lay a finger on your little friend. You have my word as a gentleman."   
  
He laughed a bit hysterically at that.   
  
"So we are agreed?"   
  
"Yes! I promise!"   
  
"Very well. We'll seal our bargain with a kiss."   
  
"Yes, please, anything!"   
  
I continued stroking him until I knew he was close, and then bent my head to take the tender head of his cock in my mouth, sucking and tonguing the sensitive crown as he thrashed wildly against his chains. He could not hope to fight my pleasurable assault though, and within seconds his warm semen was flooding my mouth.   
  
When he was empty and hanging limply in his bonds, I surged up and claimed his mouth in a filthy kiss, feeding his ejaculate back to him. He tried to jerk his head away, but the iron chains allowed him little room to retreat, and in any event I was gripping his hair tightly to hold him in place.   
  
He swallowed my offering, grimacing, as I pressed my body close against his naked flesh.   
  
"And now our pact is sealed," I murmured against his lips. "And now you have been properly kissed."   


I removed my own clothes then, setting out my suit and button-down for Elise to run to the dry cleaner on Monday, placing everything else in the hamper, all while Peter swayed, exhausted, from his wrists. He licked his lips, face scrunched up adorably with distaste, and asked for a glass of water.    
  
"After I've fucked you, love," I said. "Don't you enjoy the taste of your release on your tongue?"   
  
He shuddered delicately and shook his head. "No, Sir."   
  
"Semen is rather an acquired taste," I allowed. "Much like coffee." I retrieved the lube from my bedside table and then sat on the mattress behind him to ready his ass for my cock.   
  
His round, pert buttocks looked absolutely delectable so close to my face, and I gave in to temptation, leaning close to bite the swell of his left cheek, causing him to jump and rattle against his chains.   
  
"Such a perfect ass," I said with admiration. "I thank the Father every day that you lost your temper with Professor Quill last month, you know."   
  
He snorted at that. "You make me want to believe in God. If anyone deserves eternal hellfire, it's you."   
  
I chuckled, feeling magnanimous since I had, after all, won the battle and the war.    
  
"Time will tell, I suppose." I slid two slippery fingers into his ass, tight as a virgin's again since I had not used it in weeks. His muscles clenched in an automatic reflex to expel the intrusion, but then he forced his body to relax.   
  
"There's a good boy," I said approvingly. "Just relax and let me ready you. Legs further apart, please."   
  
As I worked him open, I tried to decide how I would take him. I was suffering as the proverbial child in a candy store suffers; too many options presented themselves to me now that we weren't hampered by time or the constraints of my office. Too many options and each more intriguing than the last--he was such a marvellously flexible boy, after all. I could bind him over the leather ottoman in the downstairs study and rut him like a stud breeding a bitch, or simply chain him spread-eagled to my bed. I could stand him on his feet and then bend him in half, wrists connected to his ankles, a position that would place stress on his muscles and cause fine tremors to run through his body the longer he strained to hold the position.   
  
Ultimately, I decided those possibilities could be explored later. On this night it was important for Peter to prove to me that he was indeed going to be as compliant and enthusiastic a lover as he'd sworn to be while in the throes of his distress only a short time ago.   
  
When he was thoroughly oiled and ready for me, I stood and unhooked his chains and then ordered him to climb onto the mattress facing the head of the bed. The bed posts had been sculpted into a wonderfully useful spiral design, ensuring that I could attach cuffs at any point along the height of the rail and they would not move more than a half inch up or down.   
  
I reattached his manacles so that his arms were still stretched to either side, but low enough now so he could kneel astride my lap on the bed, then plumped up some pillows so I could recline comfortably against the headboard while watching his every movement. Then I took my place beneath him.   
  
"On my lap, there's a good boy. Tonight, you are going to ride my cock. You are going to do most of the work, in order to prove your willingness to continue our arrangement."   
  
He bit his lip. "I... I'm not sure what to do, Sir."   
  
I slicked up my cock and aligned it with his entrance. "Slide down, just so, let gravity do most of the work."   
  
He groaned in discomfort, his thighs trembling with effort to slow his progress, until with a grunt of impatience I pulled him all the way down. He squeaked as I sheathed myself fully inside him.   
  
"Now use your legs to push yourself up, not too far, that's good." I guided his up-and-down movements with my hands a few times before I folded up my arms behind my head so I could simply watch and enjoy his performance.

The muscles of his thighs and abdomen strained as he slowly raised and lowered himself on my cock. Without the use of his upper-arm strength to provide any sort of ballast, his rhythm was faltering, and the slow, slick glide of his tight ass on my cock was the most exquisite of tortures.   
  
"If your arms were free, I would expect you to be able to move faster, to provide caresses and touches, your hands on my balls to speed things along and such," I said. "But you've behaved very badly today, Peter. I'm in no hurry to 'get it over with,' as you might say."   
  
He blew out a breath, causing a delicate curl of his hair to fall across one eye in a most beguiling manner. "I'm sorry, Sir."    
  
As his ass worked my cock, his face grew red with exertion, the fine sheen of sweat that broke out only enhancing his features.   
  
"Now rock your hips for me, back and forth, yes, like that." I watched greedily as his exhausted body struggled to please me.   
  
"Please, Sir," he begged after no small amount of time had passed. "I can't, my legs..."   
  
"You can, though, because I will it so." Idly I began tugging and twisting his nipples, then touching him until his cock plumped in my hands.   
  
"You are so beautiful like this, Peter. If only I could always be buried in your sweet ass."   
  
His eyes drifted off into the middle distance as he continued writhing on my cock, and I swatted his rump. "Eyes to me, Peter. Always to me."   
  
He gazed at me helplessly, his shoulders shaking from being held away from his body for so long and his thighs quivering, until he collapsed forward onto my chest, unable to lift his body any more. I took pity on the lad and took over for him, gripping his hips and lifting him bodily up and down on my cock.   
  
"You are truly repentant for the grief you caused me today?"   
  
"I'm so sorry, Sir, please," he panted.   
  
I wrapped my arms around his back then, hammering upwards into him with the force of a pneumatic tool. As I drove into his helpless body again and again, finally ready to chase my release, I slid one hand between our sweaty bodies to grip his own cock, and when I finally came it was to the sweet music of his breathless cries.


	3. Chapter 3

**Notes for the Chapter:**

> Skip Westcott makes an appearance in this chapter. Skip is a character from the Spider-Man comics who sexually abused Peter Parker in a PSA comic about child molestation. You can guess why he is in this story.

I could not remember ever spending a happier weekend in the company of one of my young lovers!   
  
That first evening, after I was satiated, I unchained Peter and cleaned the sweat and semen from his aching, wrecked body with a damp cloth. I cannot say for certain whether he slumbered at all that night as I held him close to me, but I myself slept the dreamless, innocent sleep of a babe in arms.    
  
In the morning I made us both scrambled eggs, which he moved about his plate listlessly, and then led him to the shower. I soaped him thoroughly, paying special attention to his reddened hole. He flinched as I played with his sore body, but he did not push me away, and when I chided him for not thanking me properly for his breakfast, he sank to his knees and sucked me as the warm spray washed over us.   
  
The following afternoon was wonderfully domestic; I sat in my favorite leather chair in front of the fire, catching up on several days worth of newspapers, while Peter knelt naked at my feet studying for a History examination. After a time I had him stand up and cuffed his wrists behind his neck, then proceeded to quiz him on the events of the French Revolution. Correct answers were rewarded with a few strokes of my hand on his cock, while incorrect responses were met with a switch to his ass.    
  
He is, as I've mentioned, a studious boy, and in time I strayed from the course material, which he knew rather well, to information I was sure Professor Rogers had not covered in the curriculum, so that his bottom was quite covered in pink stripes by the time his study period was over. His eyes blazed with hatred when he caught on that I was no longer quizzing him from his text, but he held his tongue nevertheless.   
  
When we were finished with his homework, I bent him over the ottoman and fucked him yet again, then unchained his wrists so he could once again stroke himself to orgasm for my amusement.    
  
On Sunday afternoon I chained him spread-eagle to the bed and lavished attention on his perfect body with my tongue. He was particularly distressed to be introduced to the pleasures of oral-anal stimulation, both giving and receiving, but he took to that lesson as well as his others, following my instructions absolutely and keeping his thoughts to himself.   
  
Through it all I bent him over every possible surface in my home and fucked him until his limbs were trembling with fatigue and his mouth and ass had been well and thoroughly used.   
  
It was with a heavy heart that I finally allowed him to shower one last time Sunday evening and then dress to leave.   
  
"One final thing before you return to your dorm, Peter. I have a present for you."   
  
He looked apprehensive as he reached out to take the wooden box I extended to him. When he opened it his expression was blank with incomprehension at first, until he realized what he was looking at.   
  
"I expect you to be thoroughly prepared for my cock before each of our sessions from now on." I gestured to the box of anal plugs in graduating sizes, one outfitted with a cunning series of knobs that would make his afternoon classes most unbearable.   
  
"They are each numbered, and I will let you know which one I expect you to be wearing when you arrive at my office."   
  
"But, my roommate..."   
  
"Will notice nothing, I'm sure. I know you can be discreet and keep that box hidden away, our little secret."   
  
"Yes, Sir."   
  
He slipped the box into his satchel and turned to the door, no doubt eager to be relieved of my attentions for a few hours.   
  
"And Peter? I expect to hear nothing more about this flirtation of yours with Ned Leeds, or I will be most displeased. Are we quite clear?"   
  
He swallowed hard.   
  
"Yes, Sir. I won't see him outside of class anymore."   
  
"That's my good boy. Off you go."

* * *

The students and faculty of Midtown were under the impression that Peter's internship duties mainly entailed acting as my researcher and secretary while I composed a book on the education of adolescents (which was at least partially the truth, as you'll no doubt realize if you are reading this account!) 

This white lie made it easy to have student runners slip Peter carefully coded messages from me as he sat in his classroom. If he received a note that said "the fourth paragraph needs to be fact checked," for example, he knew to show up to my office wearing the number four plug in his bottom. This system caused me no end of amusement as I imagined his mortification upon reading such instructions in a classroom of his peers; I only regretted that I could not be present to witness his discomfiture first-hand.   
  
Christmas arrived, and I orchestrated matters so Peter would return early from his family home to spend another long weekend chained to various pieces of furniture in my lodgings. On our first night, after I'd confiscated his clothing, I presented him with his Christmas gift. No doubt remembering the last present he'd received from me, he opened the gaily wrapped parcel with no small amount of trepidation, and his mouth twisted into a moue of distaste as he withdrew the silver circlet from its box.   
  
"You will wear this around your neck until your graduation, Peter, to remind you that you belong to me."   
  
"Doesn't this violate the student dress code?"   
  
"Don't be silly; it will be concealed by your shirts. And besides, plenty of students wear a crucifix or St. Christopher's medal beneath their uniforms."   
  
"Yes, but this isn't a necklace," he said flatly. "It's a collar."   
  
"I believe the technical term is 'choker.' Traditionally worn by women, yes, but then that is of little matter."   
  
I fastened it about his slender throat, and the sight of the silver collar--for of course, that's what it was--against his pale skin caused my cock to grow quite hard in my pants.   
  
"Thank you, Sir," he said tonelessly.   
  
"Now, Peter," I admonished. "I was under the impression that the school you're so set on matriculating next fall was to train you for the cruel and competitive world of development and research. Surely you can feign happiness more convincingly than that."   
  
He closed his eyes briefly, and when he opened them again his face was transformed by a wide smile the likes of which I hadn't seen since it was directed at Ned Leeds as they sat together in the student cafeteria.   
  
"Thank you Sir," he said breathlessly as he threw his arms around my neck. "I love it, I'll never take it off!"   
  
I confess, I was momentarily undone by his dazzling smile and the manufactured sparkle in his eyes.    
  
What would it be like, I wondered, to have Peter's genuine adoration directed at me in such a manner, so freely and fully given?   
  
Unsettled, I turned away to compose myself, ordering him to place the cuffs around his wrists and ankles.   
  
I strung him up on my bedposts that night and then flogged him until he begged for mercy, completely enchanted by the marks the silken tassels created upon his flesh. Then I used his ass most roughly, and while I do not believe he was significantly injured, he did walk with a slight limp over the rest of the break. 

Winter stretched out before me, a dismal, endless parade of sunless days filled with bored instructors and insolent students. After so much time spent in Peter's company over the holidays, it was difficult to return to having him to myself for only a few afternoons a week and the occasional Saturday night.

In late January, during one of those peculiarly warm afternoons New York was rarely gifted with in midwinter, I stood at my window dictating a letter to Elise and watching the students milling about on the quad. Peter was sitting by himself on a stone bench, his eyes closed, his lovely face turned up to the sun, and he looked positively angelic. I glanced at the clock and saw that as I'd suspected, he should have been knocking upon my door at that very moment.    
  
He sat there for nearly a quarter of an hour as I watched, trying to summon either the courage to come see me or to outright defy me, of which option I couldn't be certain. When a group of students walked past him I saw Ned Leeds raise a hand to Peter in tentative greeting. Peter turned his face away and said nothing, and Ned walked on, glancing back over his shoulder once and looking rather like a confused puppy who'd just been swatted with a rolled-up newspaper.   
  
I was glad to see Peter was following this directive at least, though his tardiness was wholly inexcusable.   
  
Peter watched Ned walk off surreptitiously and then drew himself to his feet, trudging towards the administration building. I dismissed Elise for the day and awaited his arrival.   
  
"You are late," I said unnecessarily when finally he entered my office.   
  
"Yes, Sir."   
  
"Do you know what the punishment is for keeping me waiting?"   
  
He sighed. "Same as every other day?"   
  
"Have you grown weary of our arrangement, Peter?"   
  
"No, Sir. Just weary."   
  
Well, that I certainly had a remedy for.   
  
"You're dismissed for now. Go on, out of my sight. I'll expect you at my quarters tonight no later than 7:30."   
  
He looked uneasy then, assured in the knowledge that any punishment I carried out in my home would be significantly more terrible than what I could accomplish behind my office door on campus, but he gathered his things and turned to go.   
  
"I'm sorry, Sir. It won't happen again."   
  
He was quite right about that.

At 7:30 on the dot he rang my doorbell, and I ushered him into the kitchen.

"Clothes off, bend over the chair back." He was trembling, his earlier ennui replaced by cold terror, and he hastened to obey. I bound his arms behind his back, wrists to opposite elbows, and ran a hand through his soft brown hair until it stood up at odd angles.   
  
"Tell me, Peter, do you know much about horses?" I asked as I picked up a large ginger root and set about peeling its tough exterior over the kitchen sink.   
  
"No, Sir. We live in the city."   
  
"As it happens I grew up with horses. Tennessee Walkers; magnificent beasts. Known for their sprightly gait. My father showed them; they were his pride and joy."   
  
He turned his head awkwardly to watch as I finished peeling the ginger and then began carving it into the proper shape. I could see his thoughts churning as he tried to work out what I was up to and how much pain it would cause him.   
  
"Show horses are not so very different from schoolboys, Peter. They lose their spark sometimes. They grow 'weary,' as you might say. And do you know how trainers get them to step lively again?"   
  
"No... please Sir, whatever you're going to do..."   
  
I turned to him and held out the ginger root. "They call it figging, Peter. Just a pinch of ginger root in the horse's rectum and suddenly your 'weary' horse is a contender for Grand Champion."   
  
"Please, no," he moaned, though he could not have possibly understood what level of misery he was in for.   
  
"We have an agreement, Peter, and I've held up my end of the bargain. Your future assured, your aunt happy, Ned Leeds safe as houses, and so forth. But I will not tolerate any more days like today where you are tardy, where you are 'weary.' And I know how to make you step lively."   
  
I wet a finger in my mouth--oiling his passage would have dulled the effect I was aiming for-- and slid it into his bottom, checking that he was stretched enough. Then I inserted the ginger root up to the precautionary flange I had carved and stepped back to watch as it took effect.   
  
The effects of ginger on the mucous membranes are not instantaneous; Peter might have thought for a blessed few moments that this punishment would indeed be the same as any other day. Then the burning sensation in his channel began to intensify, and he cried out.   
  
I watched with fascination as his buttocks tensed as though to remove the intrusion, watched as each flex of his ass called forth more and louder cries. For the sinister truth is that the ginger causes the muscles to clench, and each clench intensifies the agony of the ginger, in a wondrously wicked loop.   
  
Peter was openly sobbing now, begging me to take it out, but I had only just begun tonight's punishment. I picked up a wooden stirring spoon and then his suffering truly began.   
  
With each blow his ass squeezed more stinging juices from the root, and he would thrash against his bindings. At one point I feared his violent writhing would turn my kitchen chair into a pile of tinder, but it held.   
  
After a significant amount of time had passed, and his bottom was the luscious shade of a Bing cherry, his pained moans subsided into sniffles and his body quieted.   
  
Then I withdrew the ginger, carved it anew so its fresh juices were released to the surface, and began his torment again.

What a sight he was, squirming in his bindings and begging for relief! When I could contain my desire no longer, I removed the root and undid my trousers, slipping on a prophylactic I'd purchased specially for the occasion. Then I oiled my hard cock and slid into his burning, twitching hole. He cried out, pleading for mercy, his hole as tight as it had been our first night together as the irritant caused his channel to constrict and twitch. The rubber denied my cock some of the sensations it was used to, and so I was able to fuck him for quite some time before I achieved my climax. Through it all he flailed and begged, his breathless moans only spurring me on to greater heights of desire.

When I came, at last, it was with a growl that was both unseemly and animalistic. Then I reinserted the root and told him he would keep it in for another hour, when it would be time for him to return to his room.    
  
I gathered Peter's limp form into my arms and removed him to the sofa in the next room, where I held him while he sobbed against my chest, promising never to be late again for one of our appointments. It was a promise that I can assure you he kept.

* * *

There was no doubt in my mind that Peter hated every minute he was forced to endure in my company, but he was, after all, a 17-year-boy, and had begun to grow rather addicted to the constant orgasms I wrested from his young body. I made a game of masturbating him to climax repeatedly until he was delirious with heightened sensitivity, and then a new game of seeing how long I could keep him on the precipice of climax without release. He retained his stubborn streak, and so could hold out for some time before he gave in and begged me with liquid eyes to let him come.

But give in he did, every time. On one such occasion I set him on my desk with his legs propped up against the arms of my chair while I fondled him to hardness, then set about teasing him mercilessly. I stroked him with slick fingers until he was thrusting into my hand, and then withdrew and watched him hump the air with dissatisfaction. When he had calmed somewhat, I started the process again.    
  
His frustration was delightful to behold, nose scrunched in irritation while his body twisted and squirmed.    
  
"Please Sir," he breathed softly, "please I can't take much more..."   
  
"Of course you can, dear boy." I added a fresh application of lubricant to his already slick purple cock and stroked, quickly, no more than five times before pulling away.   
  
"Please Sir, I can't!"   
  
It took longer each time to calm his body down enough so that I could touch him without bringing him off prematurely. He lost all self control at one point, his fingers daring to brush his cock against my orders, and I grabbed his wrist firmly, assuring him his hand would meet my ruler for the transgression.   
  
When I judged that he truly could hold off no longer, I stroked him five, ten times. He let out a low moan as his pleasure built, and then I withdrew my hand a final time, watching in fascination as his bobbing cock twitched and spurted, untouched, while Peter groaned in distress at being denied a truly euphoric release.    
  
"Why?" he asked pitifully after he had recovered from his wholly unsatisfying orgasm. "I don't even want to and you make me want to, why?"   
  
"Why does the cat play with the mouse before its meal, Peter? Because it can."   
  
He lowered his head, denying me the sight of his tearful eyes, and I smacked his sore cock in retaliation.   
  
A few days later, I noted that his cock was slower to perk up under my attentions, and deduced that he was trying to masturbate before our sessions to deprive me of his needy cries.   
  
"Peter," I said with consternation. "You know full well that you are not to touch yourself except in matters of hygiene, unless directed by me."   
  
His eyes flashed defiantly, his stubborn jaw set, as he said, "You can't prove I've done anything wrong. It's not my fault I find you so repellant."   
  
I continued to stroke him until he was fully erect, then ordered him to his knees to tongue me, as I plotted my next move.

* * *

On St. Valentine's Day, I presented him with a new gift, which he opened with trembling fingers. In the box lay a sturdy steel ring and a curved steel cage that rather resembled a bent kitchen whisk.

"What…what are those?" he asked, his voice betraying the slightest tremor.   
  
"You are about to find out, dear boy. Remove your clothing."   
  
When he stood once again pale and naked before me, I slid the steel ring around the base of his testicles.   
  
"Sir?" he asked fearfully. I ignored him and placed the cage over his cock, and then I locked the two pieces together, securing them with a tiny padlock. Then I showed him the key, which was concealed by my clothing on a chain around my neck.   
  
"You'll not disobey my orders again, Peter," I said firmly. "Your cock belongs to me until the end of the school year."   
  
"Whatever," he said, crossing his arms sulkily. "Now you can't make me do that anymore, big deal." His language was so wonderfully prudish when he was not in the throes of pleasure or pain, it was a source of constant merriment for me.   
  
"Indeed?" I asked with an arched eyebrow. I stretched him out on my desk then and oiled up his ass, tugging at his balls and watching as his cock tried valiantly to swell. It did not take long before he was squirming in distress, and when I fucked him that afternoon he played the willing lover to the hilt, his body opening hungrily to me, his hands clenching my back as he sought release from this new torment.   
  
"Please Headmaster, it hurts," he cried as his eyes welled with tears. "Please take it off'!"   
  
"Tomorrow, perhaps," I murmured as I thrust into him. "If you are very good."   
  
When I was finished I slid down his body and pressed his knees to his chest, the better to lick my release from his pretty pink hole, and the sensations of my tongue on his quivering ring of muscles drove him into quite a frenzy of unsated lust.   
  
And when I kissed him deeply, he was so overwrought with desire he kissed me back with none of his usual distaste.   
  
He was beside himself, and when I'd dressed I pulled him onto my lap and stroked his back soothingly while we waited for his body to calm down enough so that he could join his classmates at dinner.   
  
I'd meant to use the chastity cage only the one time as a corrective measure, but I'm sure I don't have to tell you that I became quite enamored with this new Peter, who sought to please me in all ways so that he might be allowed to achieve an erection and subsequent release. As time passed I used the cage with more frequency and kept him in it for longer periods of time.   
  
The key remained about my neck, and I knew beyond a shadow of a doubt that his body was mine completely. He even tried skipping an Academic Decathlon meet once, appearing in my office unscheduled and pleading for the chance to orgasm, and though I was severely tempted by the idea of having Peter to myself for an unscheduled afternoon, I sent him back to Professor Harrington with a sore bottom and a firm admonishment about skipping his extracurriculars.

March brought with it news of Peter's acceptance to MIT he wanted so desperately to attend, as well as several other good schools located around the country. I told him we would celebrate when he returned early from his two-week long spring break. He begged to be allowed to come just once before he left, but I patted him on his lovely rump and sent him off to the train to visit his family, the key to his cage around my neck.

He was to remain at home for 14 days, the longest stretch by far that I enforced his chastity, and he was given explicit instructions to finger himself and wear his plugs at intervals while he was away.   
  
Thus, I was not terribly surprised when he showed up at my quarters fully two days before his expected arrival, pounding on the door and begging me for release from the infernal device.   
  
I opened the door and he dashed inside, shrugging out of his rain gear as breathless pleas tripped from his tongue.   
  
"Headmaster, please, it hurts so much, I can't, every night it wakes me up..."   
  
He froze, however, when he realized that I was not alone.   
  
One of my dearest friends, a public school teacher with an unholy interest in the 'student body' like myself, had journeyed from Tennessee to grace me with a visit while our favorite students were away over the break. He was seated in my parlor sipping a cup of tea as the spring rains battered the windows of my home when Peter entered the room, more disheveled than I'd ever seen him.   
  
My friend stood and approached the boy, a slow smile spreading across his face.   
  
"So this is your Peter," he said. "Your praises scarcely did him justice, I think."   
  
"I'm sorry, Sir," Peter said as he stared at his muddy boots. "I didn't know you had a guest."   
  
"Nonsense, Peter," I said. "This is a dear friend of mine, who will be most happy to make your acquaintance."   
  
"I can just return to my dorm now..." Peter said.   
  
"No, I don't think so. I had not anticipated sharing our time together, but this is too fortuitous an opportunity to pass up. Please remove your clothing, Peter."   
  
His eyes strayed longingly to the front door, but he was too well-trained by this point in our acquaintance to offer resistance. Within seconds he was naked save the silver choker and steel chastity cage.   
  
My dear friend, Skip Westcott, looked on with appreciation.   
  
"He is more finely built than my Harley," Skip said. "But his delicacy is quite lovely in its own way."   
  
"Indeed," I said with pride. "And you'll never meet another boy who looks so lovely when he cries. Bend over, Peter, and show Skip your pretty, pink hole."   
  
Peter looked to me, silently pleading to be released from this humiliation, but I gestured impatiently for him to do as he'd been told. Face red with shame, he bent over the armchair and exposed himself to my friend's interested gaze.   
  
Skip caressed the pale globes of his buttocks and then spread him wider with his thumbs.   
  
"He wore this on the journey?" Skip asked as he twisted the plug in Peter's ass. "No wonder he's nearly out of his mind."   
  
"He was instructed to show up ready for my use," I said.    
  
Skip pulled out the large plug with a flourish and replaced it with one of his fingers. Peter mewled piteously when his finger found Peter's prostate.   
  
"Have you considered milking him?"   
  
"I have," I admitted, "but I've found that I'm too much enthralled by the look on his face when he comes."   
  
Skip continued stroking Peter's gland while the boy gripped the chair until his knuckles were white and pre-ejaculate was liberally coating the bars of his cage.   
  
"Are you going to make him wait until his scheduled return?" Skip asked.   
  
"Please, no, Headmaster please," Peter begged. I smiled to think how far he'd come from the sharp-tongued boy I first met.   
  
"I probably would have if you had not turned up," I said. "But now I think allowing him to orgasm after such a long wait might render him relaxed enough that we can both take our pleasure in his ass together. If you're so inclined, of course."   
  
Skip laughed. "You certainly needn't ask twice. Shall we go upstairs?"

We retired to my bedroom, which was delightfully cozy in contrast to the growing storm outside, and removed our own clothing while Peter nervously twisted his hands together and waited.

"Peter," I said sternly, "I will be generous today, and allow you to orgasm even though it is only Wednesday. In exchange for this generosity, I expect you to show my guest every courtesy."   
  
"Yes Sir," he said quietly, his cheeks pink with embarrassment.   
  
"There's a good boy." I placed the silver cuffs around his wrists and ankles but left him untethered for the moment, and then I took up position sitting at the foot of the bed. He started to climb onto my lap but I turned him around so he was facing Skip, his back to my chest, kneeling on either side of my thighs. Then I slicked up my cock and pulled him onto it. His body opened quite willingly after the punishingly large plug he'd been wearing during his travels, and he was fully seated with just a few thrusts of my cock.    
  
I removed the key from my neck and handed it to Skip, who knelt in front of us and began to unlock it.   
  
Peter's whole body was trembling, whether from fear or desire I could not say. Probably it was some combination of the two.   
  
His cock sprang to attention when it was freed, and Skip pumped it several times, smearing the precome around the head. Meanwhile I wound my arms through Peter's so they were pinned to my side.   
  
When his cock was quite full and still steadily leaking, Skip inserted his thumbs up beside the base of my cock, stretching Peter further. Peter bucked wildly against my chest when he realized what was to happen next.   
  
"Shhh," I soothed. "You must relax or this will be quite unpleasant for you."   
  
"I can't, it's too much," he moaned.   
  
"You can, and you will."   
  
He continued bouncing on my lap even in his fear, as his cock sought release after its long confinement.   
  
I leaned back further on the bed, resting upon my elbows, Peter's arms still trapped by my own, as Skip alternately stretched Peter's rim and stroked his shaft.   
  
"Please, no, it'll hurt," Peter cried, but his hard, red cock showed no sign of flagging.   
  
"You are indeed a generous friend," Skip murmured as he stroked Peter to an orgasm so fierce that Peter's seed landed high on his neck, almost reaching his own face. "I shall have to repay the favor sometime."   
  
Peter lay limp against my chest after he came, his body softer and more relaxed than I'd ever seen it, as Skip began pushing his cock inside Peter's body.

I am sure my skills as a writer cannot fully convey the ecstasy of this experience! My own cock was snug in Peter's channel when Skip pressed inside, and the sensation of his shaft against my own, both of us buried in Peter's tight body, was exquisite. 

We found a rhythm, our cocks brushing together as we fucked into Peter, while the boy was pinned between our bodies, his head lolling like a rag doll.   
  
"Too much," Peter mumbled, twisting to bury his face against my neck, and I realized with some surprise that it was the pleasure, and not the fullness, to which he was referring when his cock started to fatten again.    
  
"Stroke him," I encouraged my friend. "Let's see how many times we can bring him off before we have finished."   
  
Skip stroked Peter's oversensitive cock, his own rhythm never faltering, and soon the boy was spasming through his second orgasm.   
  
This time, though, Skip did not even stop to let Peter collect himself. We pounded into his ass while Skip rubbed Peter's soft penis, and for the first time Peter fought against my hold on his arms, though of course, to no avail.   
  
"Please, stop, please Sirs," Peter breathed, trying to twist out of my grasp, but Skip never stopped his stroking, and soon the sobbing boy was on the brink of his third orgasm in less than half an hour. When he came again, hot tears spilled down his cheeks, and the violent clenching of his body caused me to climax as well. Skip followed quickly, and we stayed like that for a moment, recovering, before Skip slowly withdrew, causing my own overly sensitive cock to twitch.   
  
I lifted Peter's body from my own, reached for the plug Skip had so thoughtfully brought up from the parlor, and stuffed it into Peter's lax body to hold our seed until we were ready to use him again.   
  
"He really is exquisite when he cries," Skip said. I stroked the boy's tear-streaked face and murmured my agreement, but Peter made no reply, having passed out from the intensity of the experience.

* * *

Peter slumbered for the remainder of the afternoon, only rousing at my prodding after Skip and I had hazarded the storm to venture into town for groceries. I left Skip to the task of preparing a light dinner while I steered the boy into the shower to soap his body clean of the liberal amounts of semen that coated his belly and thighs.

"Headmaster?" Peter asked quietly as I dried him with a towel. "Could I have something to wear to the table?"   
  
My first instinct was to decline his request, for I so enjoyed his humiliation at being constantly, lewdly displayed while in my home, but he had been a very good boy so far this afternoon, after all, and so acquiescent to the addition of a third party in our games, that I relented.   
  
"You may wear this," I said, pulling a white Oxford from my closet.   
  
"Thank you, Sir," he said as he slipped it on. I stopped his fumbling fingers and secured only the center button. The shirt was, of course, much too large on him, the cuffs dangling almost to his fingertips and the collar sliding off one shoulder, making him look even younger than usual and only enhancing his lovely vulnerability.   
  
At dinner, Peter nibbled at his food while darting wary glances at Skip, who was regaling me with stories of his own favored student, a slim blond named Harley who was apparently quite susceptible to hypnosis.   
  
"I realized it by accident, of course," Skip was saying, "but once I saw the potential for molding him more completely, I was quite unable to stop myself."   
  
"How do you do it?" I asked. Skip pulled out his watch chain and spun the clock face around. I saw Peter glance up at it and look away quickly.   
  
"He's convinced he's in love with me now, and I don't think he was at all interested in the company of men before," Skip said. "And now if I ask him to 'fetch' me something, he drops to the floor and begins acting like a puppy!"   
  
Peter began to look rather queasy at this point in the conversation.   
  
"And he looks so becoming on the end of a leash," Skip concluded, "that I'm rather tempted to hold him back a year."   
  
"I find that most boys' features are enhanced by a leash," I said, and we both chuckled.   
  
"I could try hypnotizing your boy if you're interested," Skip offered as he finished his glass of claret.   
  
Peter stared fixedly at his plate, only the trembling of his fork giving away that he was listening to our conversation and awaiting my answer.   
  
"Perhaps," I said thoughtfully, though I had no real intention of allowing Skip to put the boy under a spell. While the idea was intriguing, I doubted it would work with Peter and, at any rate, I rather enjoyed his little sparks of defiance. "It is very kind of you to offer," I said, winking at Skip, who understood at once that my answer was no and that Peter need not be privy to this knowledge.   
  
Once the table was cleared we adjourned to my bedroom, where I presented Peter with a choice as to how we would spend the rest of the evening. In one hand I held my own pocket watch, and in the other a Polaroid camera.   
  
Peter paled as he looked between the items.   
  
"I suggested, and my guest happily agreed, that we should like you to pose for us this evening in a series of photographs. But of course, it is your decision."   
  
I had gambled—correctly—that he would not be able to agree to the violation of his mind on top of the violations I perpetuated upon his body, no matter how desperately he wanted to avoid committing our indiscretions to film.   
  
"What would I have to do?"   
  
"Whatever I say, Peter. Think of it as a performance."   
  
"And you won't show anyone?"   
  
"Of course not; these photographs would be far more damaging to us than to you." I did not, of course, tell him that we would be careful to frame the shots so Skip and myself would remain unrecognizable.   
  
Peter looked between the two items and finally, with great reluctance, pointed to the camera, no doubt horrified at the possibility of being forced to act like a dog for our amusement, or worse, being compelled into having actual feelings for me, but still he looked most unhappy with his choice.

While he huddled anxiously on the bed, Skip and I brought in several floor lamps from other areas of the house so the room was properly illuminated.

"I must test the lighting first," I said, snapping a quick few pictures. As I watched the instant photos develop, I ascertained at once how photogenic Peter was, how well the camera captured his features as the light and shadow played across his face, highlighting his button nose and small mouth, and I decided I should prefer to use my 35mm camera, for the quality would be much greater, even though the images would be in black and white and not instantly viewable. I handed off the Polaroid to Skip and retrieved my other camera, already plotting when I could best make use of Midtown's darkroom without garnering unwanted attention.   
  
"Kneel on the bed, Peter, that's good." snap "Now spread your thighs. Eyes to me."   
  
He looked directly into the camera and bit his lip nervously.

_ Snap. _

"Lean back further, good. Pull the shirt off your shoulder, there's a good boy." I zoomed in on his long neck and the curve of his jaw.

_ Snap. _

"Unbutton the shirt, now give me a smile so I can see how much you're enjoying this."

_ Snap. _

I paused for a minute to collect a length of chain from the trunk by the window. "Our guest is partial to boys on leashes, Peter. If you would be so good...?"   
  
With shaking hands, he clipped one end of the chain to his collar and the other to the footboard while I resumed capturing his movements.   
  
“Remove the shirt. Turn away so we can see your pretty bottom.” He knelt on the bed facing away from me and then turned to look over his shoulder. The contrast of the hard chain trailing down his soft flesh caused my cock to swell in my pants.   
  
"Spread your cheeks."  _ Snap. _ "Now turn to me again and touch yourself," I ordered. His hand played with his cock in a desultory fashion, and I sighed. "If you are not enjoying this I might as well lock you up again, yes?" His eyes flashed angrily but he brought himself to hardness as the whirring clicks of the two cameras documented his every move.   
  
"Skip, would you like to join him now?"   
  
"I'm sure I should like nothing better," Skip said as he removed his clothing.   
  
Skip abandoned the Polaroid and seated himself behind the boy.   
  
"Spread your legs, Peter. Wider."

_ Snap. _

As Skip began stroking Peter's shaft, I instructed the boy to look into the camera lens again and show us how much he was enjoying the attention. He lowered his head and directed a heated look straight at the camera as he thrust shamelessly into Skip's hand.   
  
"Very good," I said, my voice thick with desire. "But I don't want you to come just yet. Why don't you attend to our guest first?"   
  
Skip stretched out on his back with his feet towards the head of the bed so I could more easily photograph Peter's face as he swallowed Skip's cock.   
  
He was a natural at taking direction and finding the source of light, and I dearly wished I had a movie camera on hand, although developing that sort of motion film was well beyond my capabilities. He worked at Skip's cock as well as any professional, and Skip had to push him away after a few moments before he climaxed too early in the proceedings.   
  
"Good boy. Now tend to yourself."   
  
He knelt back, legs straddling Skip's thighs, while he worked his cock with his hand. When he was very close to his release, I ordered him to stop so that I could load another roll of film. He huffed with annoyance but did as I said, scowling at me while his cock bobbed hungrily.   
  
"Now stroke yourself again. Work a finger into your slutty hole as well."  _ Snap. _ "Now another. Two cocks at once today, Peter, you are sure to be the toast of MIT."   
  
He glared at me as he rode his fingers and stripped his cock.   
  
"And smile, Peter. I want to believe you're having the time of your life."   
  
Once again I watched in fascination as Peter's angry visage was transformed into a smiling mask. He flirted with the camera as he brought himself ever closer to his climax, thrusting into his fist, working his slender fingers into his ass, arching his back when Skip began pinching his nipples.

I'm sure I spent a whole roll of film trying to capture the ecstatic expressions that played upon his face as he jerked himself to completion.

When he was finished I traded places with Skip so that he could undertake the photographer's duties. I repositioned Peter on his hands and knees while Skip placed himself to the side of the bed to best frame our coupling.   
  
I stood at the foot of the bed, one hand twining about the chain so I could pull his collar tight against his throat. He gasped for air as I fucked into him ruthlessly, his ass clenching hotly around my cock.   
  
I pulled out abruptly, still achingly hard, and ventured into the spare room once more to retrieve my tripod while Skip continued to issue instructions to the boy.   
  
"Arch your back," I heard Skip say as I adjusted the camera mount. I paused to watch Peter shift on the bed, directing a sultry look at the camera.   
  
"He'd make a pretty little kitty," Skip murmured, and Peter looked away quickly.   
  
I took the camera from Skip and placed it atop the tripod, angled the camera so it was pointed at the foot of the bed, and set up the shutter release cable.   
  
"Sit here Peter," I said pointing between the two tall foot posts. "You're going to take care of us both with your slutty mouth."   
  
When I was certain the camera was correctly positioned, we stood to either side of the boy, our cocks aimed at his lips.   
  
"Make it good, Peter," I warned.   
  
He opened his mouth and sucked at the head of my cock, then Skip's, bringing his hands up to stroke us as he worked. Soon his lips were messy with saliva and pre-ejaculate, swollen and red, as he desperately tried to bring us off and end his current predicament.   
  
"Surely I've taught you better, boy," I said, as I continued clicking the cable. He redoubled his efforts, fisting our shafts as he turned from one cock to the next, trying to fit us both in his mouth at once. I noted with surprise that he had become semi-erect again with no external stimulation.   
  
"Look to the lens, Peter," I said, and as he stared into the cold eye of the camera, we both came simultaneously, coating his lips and tongue and cheeks with our release.    
  
When we had returned order to the room, I climbed into bed and pressed my naked chest to Peter's warm body. Skip made to retire to the guest room but I tsked.   
  
"We've shared everything else, friend. Stay with us; you might feel up to making use of Peter again in a few hours."   
  
Skip agreed and climbed in next to Peter, who pushed himself back against me. I laid a hand to Peter's chest and felt the rabbit-quick beating of his heart, and smiled.   
  
I awoke at dawn to the sounds of Peter's soft cries as Skip pistoned into his ass, one hand wrapped in Peter's soft hair and the other pulling at the chain still attached to his throat, and though I was loathe to leave my warm bed and Peter's body, I made myself rise and dress so I could make use of the empty campus to develop my film.   
  
I walked briskly through the empty corridors to the East Wing, where the art classrooms were situated, pausing briefly to look in at the empty chemistry lab where I had once lurked to watch the clever boy focusing on his work, his face set in concentration.   
  
I moved quickly and efficiently to set up the darkroom. I planned only to develop the film this morning and print up one or two keepsakes for Skip, though I could tell from scanning the negatives that most of the images were of excellent quality. I printed out only a handful, each more erotic than the last--Peter touching himself, Peter displaying his abused hole, Peter arching his back as he stared at the viewer, Peter struggling to bring us off with his hands and lips.

And one image, a close-up of his face so arresting that I drew in a sharp breath. I have never fancied myself more than an amateur photographer, but I had managed to capture perfectly the moment when Peter's mask fell, and it was all there in his eyes: his lost innocence; his shame and humiliation at being ordered to perform for us; his confusion by the way his body betrayed him and grew aroused at the rough treatment, and a longing to return to the boy he'd been in September, before he ever fell into my clutches and learned there was so much worse to fear in the world than the attentions of a confused bully named Flash.

His expression was captivating; it was heartbreaking.   
  
And if you think this image caused my own predator's heart to thaw, to feel some pity for my captured prey, then I'm afraid I have not adequately conveyed my depravity through these writings.   
  
I removed the damp photo from the line where I had clipped it to dry and masturbated furiously as I stared into Peter's haunted eyes, coming quickly and splattering the photo with my release, causing the chemicals to run and distort the photo in a grotesque mockery of Peter's pain.   
  
It was, to be sure, my favorite image from our little impromptu photo shoot.   
  
I treasured it.

**Notes for the Chapter:**

> I hope you enjoyed this chapter. Please leave a comment if you did :) Last chapter tomorrow.


	4. Chapter 4

April ushered in the beginning of the end of the school year, and I was once again forced to chaperone the yearly Spring Formal held jointly by Midtown Prep and Miss Romanoff's Finishing School. A misery under the best of circumstances, made utterly insufferable by the presence of the woman herself Natasha Romanoff, the Principal at our sister school, who sidled up to me at one point to make some rather alarming insinuations about my overt interest in watching her young ladies dance.   
  
She was wrong, of course; she had mistaken my watchful attentiveness of Peter's every move as interest in Peter's date, a unassuming girl named Michelle. Still, that Miss Romanoff had detected anything untoward in my behavior at all put her leagues ahead of our colleagues in her terribly accurate assessment of my predatory nature.    
  
It was unsettling, to say the least.    
  
Her snide remarks about my character would have been tolerable, though, were I not so incensed at watching Peter laugh and twirl gaily about the floor with his date, even going so far as to press a kiss upon this Michelle's dark cheek!   
  
Thankfully, before Miss Romanoff could get too carried away with her accusations, she spotted one of my students hovering suspiciously about the punch bowl and strode across the floor to put a stop to such shenanigans, leaving me to resume standing in the shadows, watching Peter dance while I seethed internally.   
  
Fueled by fantasies of throwing Peter to the gymnasium floor and staking my claim upon his ass in front of all present, I was a roiling mass of anger by the time the last dance was in full swing, and I had nowhere to direct my rage, as Peter was not scheduled to arrive at my quarters until the following day.   
  
I went home alone that night and stewed over our situation, concocting ever wilder punishments for Peter's transgressions, and when I awoke Saturday morning I felt as though I'd scarcely slept at all.   
  
The boy seemed almost chipper when he appeared at my door that afternoon, a fact that I attributed at the time to his wanton activities with Michelle the previous night. (The benefit of hindsight, of course, has led me to conclude that his cheerful mood had more to do with the lovely spring day and his ability to actually count down the hours he would be forced to spend in my presence, but at the time I was too blinded by jealousy to think clearly.)   
  
"Strip," I said coldly once he was safely inside, and Peter's pleasant mood evaporated when he noted my sour disposition.   
  
"Yes, Sir," he said as he hastily removed his sweater and started undoing the buttons on his shirt.   
  
"Tell me, Peter, did you fuck her?"   
  
"What? Who?" he asked, sounding genuinely confused.   
  
"Miss Jones. Did you fuck her? Stick your dick in her pretty cunt? Did she scream for you?"   
  
His fingers faltered as he realized how very much trouble he was in.   
  
"I...what are you talking about? We just danced! And I bought her a sundae!"   
  
"Yes, I'm sure that's all you did."   
  
"Please, Headmaster, I didn't do anything wrong!"   
  
"I told you to strip!" I shouted, and he quickly pulled his undershirts over his head, not even bothering to fold them neatly as he usually did.   
  
"I didn't do anything, I promise!" he tried again, his slender chest heaving rapidly with fear, his pretty pink nipples standing to attention in the cool air.   
  
"So you say, but how can I know for sure?" I asked. "It seems that I have been far too lenient with you these past few weeks."   
  
"Lenient!" he cried, suddenly indignant. "You've been a monster! Whipping me, humiliating me, sharing me! If that's your idea of lenient..."    
  
He trailed off when he saw that I had retrieved his wire cock cage from my topmost desk drawer.   
  
"Yes, lenient," I parroted. "I have allowed you your freedom since the spring break, but not any longer. You will wear this until the day you graduate, Peter, and you will thank me every day for it."

His eyes widened in outrage. "You told me to go to the dance! You told me to take a girl and act normal, and I did!"

"I did not tell you to wet your wick in any convenient co-ed who happened along, though, did I?"   
  
His eyes narrowed but I noted that he did not deny it any further.   
  
"Remove your uniform slacks, Peter, and put this on," I said, extending the cage.   
  
I think Peter was almost as surprised as I was when he snatched the chastity cage from my grasp, threw it to the ground, and stomped it flat with one of his scuffed sneakers!   
  
We both stared in shock at the crumpled metal, twisted beyond usefulness or recognition.   
  
And then he began apologizing profusely.   
  
"Oh please, I'm sorry Sir, I didn't mean to!" His eyes were huge, and his normally pleasing, high voice was a low moan of fright.   
  
I was positively afire with fury as I twisted his arm behind his back and marched him upstairs to my bedroom.   
  
"Insolent fool!" I snapped as I threw him face-down onto my bed. "Do you think I can walk into any dime store and replace a device such as that?"   
  
"Please, don't," he whispered, though he could not yet know what I had in store for him.   
  
"Silence! One more word out of you and I swear our agreement is void!"   
  
He lay on the bed, shaking with fear, as I pulled off his sneakers and yanked his slacks roughly down his legs. He had arrived already wearing a plug as instructed, which I removed, pausing to slide two fingers inside his body. He was warm and slick around my fingers, and I had to exercise a fair amount of self-restraint to stop myself from fucking him there and then. But my pleasure would have to wait. I flipped him onto his back, so that I could watch his face as I punished him.    
  
"Stupid, worthless little boy," I hissed. "If you move so much as a muscle your aunt's going to receive some very interesting photos in the post!"   
  
He blanched at this, for I had already shown him a carefully curated selection of pictures that depicted him sucking cock with apparent abandon, looking just as slutty and willing as any paid whore. I left him there to await his fate while I went down to the basement to gather the tools I would need for today's lesson.   
  
Several pieces of rope. A long length of pipe fitted with screws at each end. A thin rattan cane. I smiled to myself as I returned to the bedroom, where Peter awaited me.   
  
I began by binding his slender ankles together several times over with a soft rope. He looked confused, for I generally tied him in ways that would give me easy access to his luscious ass, but he had taken my order for silence quite seriously, and said nothing as he watched me work.   
  
Once his legs were secured together, I screwed the length of pipe to the holes I had previously drilled into the metal bed posts a foot or so off the mattress, and then I rested his ankles over the bar. I then tied his feet to the pipe with an additional length of rope so that he could not move his legs once I began punishing him. Finally, I stretched his arms up over his head and secured his wrists to the bedposts at the head of the bed with a final piece of rope. When I was finished, he lay flat on his back, clenching his fists nervously and twitching his raised, bound feet, watching me with ill-disguised terror.   
  
I ran the cane down his cheek, rested it against his lips, and ordered him to fellate it. He drew the end into his mouth and suckled it weakly.   
  
"Let us see how much you enjoy dancing after today's punishment," I hissed, sliding the cane further down his torso. He frowned in confusion, and then gasped in comprehension when I raised the implement and began lashing the tender soles of his feet.

I was exceedingly careful, for bastinado is an art form requiring precision to be administered correctly, and one which I probably should not have have undertaken while my blood was still boiling, but I made sure to place each stroke of the cane lightly and evenly. There are many fragile bones in the foot, after all, and even in my rage I had no wish to disfigure the boy permanently, nor to alter the bewitching sway of his ass as he moved.

He twitched and writhed against the ropes with each lash, his breath hitching between bitten lips as he fought to suppress his cries.   
  
I alternated strikes to the soles and arches of his feet, pausing after 15 lashes to see how he was coping. His hands were clenched into tight fists, his breathing was labored, and his eyes were glassy with pain.   
  
I caressed the tip of the cane along his throat. "Eyes to me, Peter."    
  
His eyes shifted from the ceiling to meet my gaze.   
  
"We are not yet halfway finished with your punishment," I informed him. He squeezed his eyes closed slowly and then opened them and nodded.   
  
I ran the tip of the cane along his soft cock, and he moaned.   
  
"You would wish me to skip to the end and fuck your slutty hole, would you not?"   
  
He nodded quickly, but I was far from finished.   
  
I left him for a moment to gather a couple more items from the bathroom: a soft shaving brush and a firm hair brush.   
  
When I began using the bristles to tickle his bound feet, he let out a shriek and his whole body jerked as though he'd been electrocuted.   
  
Satisfied with his reaction, I set myself a pattern of alternately whipping and then tickling his feet. I could not say for certain which he hated more. The caning caused him to sob and cry out in pain, whereas the tickling jolted his body so much that it was a wonder he didn't dislocate a shoulder. After several long moments he broke his silence, offering me anything so that his torment might end. His pleas only excited me further, of course, and it was a long hour of torture for Peter before I could deny my desire no longer.   
  
When his tender feet were bruised and his pleas had subsided into one long, wordless cry, I finally set aside the cane and began untying his feet. Once I had unscrewed the pipe his ankles had been secured to, I removed my clothes and climbed up the bed between his legs. His eyes were bright with unshed tears, and he let out a pitiful wail when I squeezed his sore feet firmly before bending his knees and hooking them over my shoulders.   
  
“Did you enjoy today’s lesson, Peter?” I asked as I slid into his tight channel.   
  
There was no correct answer, of course, and the poor boy bit his lip helplessly as I fucked him slow and deep.    
  
"If you did not like the abuse, why are your eyes still dry?"   
  
He finally found his voice. "You like it,” he whispered. “Like it...when I cry, and your creepy friend said…."   
  
"And so you thought to deprive me of your tears?"   
  
"I," his breath caught on a sob. "I thought to try."   
  
"Well. We'll have to see about that."   
  
I found his soft cock with one hand and stroked it; the pain in his feet really must have been intense because he was slower to harden than usual, even for a boy so thoroughly trained in finding release through torment. When he was fully aroused, I released his cock so that I could brace my hands on his pale chest while I pounded into him. It did not take me long to satisfy my lust, and when I was finished I pulled out of him, leaving him squirming on the bed, tugging uselessly at his bound wrists, aching and unsatisfied.   
  
I left Peter where he lay, my semen leaking out of his ass, while I took a long shower, washing away sweat and ejaculate, feeling the last of my tension and anger wash away with the suds. When I was finished, I tied a robe around my waist and went down to the kitchen to thaw a couple of steaks for dinner. I would grill them outside, I decided, while Peter could prepare us a salad to accompany the meal. Just the simple act of standing at the counter chopping vegetables would be a misery for his abused feet. The image of Peter dressed only in a frilly apron, shifting from foot to foot to relieve his pain, was so wonderfully domestic and erotic that I began to harden again.

I returned to the bedroom, where Peter was dozing fitfully, still partially aroused. I watched him for a moment, his eyes moving rapidly behind his closed lids, his mouth moving soundlessly. Then I ran my hands along his sides from his narrow hips up to his exposed underarms.

He jerked, and huffed out a small laugh. " _ Don't... tickles, Ned _ ." he murmured.   
  
I froze, and then I pinched his nipples quite severely.   
  
His eyes flew open, and he tried to rise from the bed before his bound wrists forced him to collapse into the mattress, groaning in pain.   
  
"What were you dreaming about, Peter?"   
  
"N-nothing, Sir."   
  
I grabbed his testicles and squeezed, and he let out a shocked breath.   
  
"Do not lie to me again."   
  
"I was..." He paused to lick his lips. "I was at the Formal. Dancing until my feet were aching."   
  
"With Mr. Leeds?"   
  
He nodded as best he could from where he lay on the bed, watching my face carefully.   
  
I untied his wrists, which were quite red and abraded, and shifted our positions so that I was reclining against the headboard with Peter sitting between my legs, his arms quite useless at his sides.   
  
"I should like you to use your mouth on me Peter."   
  
Dutifully he bowed his head and took my cock into his mouth.   
  
"Not there."   
  
He shuddered with revulsion as he bent his head further.   
  
I am certain that of all the sexually perverse acts I had taught Peter to endure and even occasionally enjoy, analinguis was the most hated. I was, of course, fastidious in my cleanliness, but it was an act so taboo, and of such an intimate nature, that he detested being forced to perform it on someone he despised as much as myself.   
  
"Dancing with Mr. Leeds,” I mused as he licked tentatively at my hole. “And in your dreams you thought Mr. Leeds would want to dance with you? He has no interest in you, Peter, if indeed he ever did."   
  
I chuckled as Peter twitched at my cutting words.   
  
"Deeper," I said. "You know what to do, do not pretend to be a novice."   
  
The feeling must have begun returning to his arms, for he gripped my legs and pried my cheeks apart with his thumbs.   
  
"I've seen your little friend often in the company of that new transfer student who joined us last year, Mr. Osborn," I continued. I felt the slightest scrape of his teeth against my anal ring, and I flicked his ear in warning.   
  
"I wonder what they are doing on this lovely spring day. Do you think they're playing together as we are? Mr. Osborn seems a worldly sort, don't you think?"   
  
The sensation of his warm, wet tongue in my ass was delightful. I threaded a hand through his hair while I continued my ruminations.   
  
"No, probably not, Mr. Leeds seems too innocent for such activities, probably not yet corrupted as you are. But perhaps they are kissing right now, or even just laughing together. You used to enjoy laughing with Mr. Leeds, did you not?"   
  
My grip on his hair tightened and he arched his body to try to relieve the pressure on his scalp.   
  
"What did you think, Peter? That Ned Leeds would run off to Massachusetts and join you after graduation so that you could pick up where you left off? Did you truly think you were still worthy of his affections after all the time we've spent together?"   
  
His tongue worked at me while his hand slid to my shaft in an effort to speed things along, but we had many hours to kill before dinner. I grasped his hand and held it tightly in my fist, grinding the bones together.   
  
"Maybe someday Mr. Leeds will indeed be able to attend a dance with another man, though I rather doubt I will live long enough to see such a sight," I said thoughtfully. Peter’s tongue entered my body again, so sweet and wet that I shivered. "But if that day should come, you will not be the one on his arm."

My cruel heart warmed to see that my words had finally succeeded where my cane had not, for his brown eyes were glistening, and as I watched, one fat tear rolled down his rosy cheek. I brushed it away with a finger that I brought to my lips.

"No, not with you, Peter. Not unless you want to wreck his innocence as surely as I have wrecked yours."   
  
He cried then, soft shuddery sobs that electrified my skin and brought me closer to climax. I sighed contentedly, patting his damp cheek, and settled myself in for a long afternoon of pleasure.   
  
"I would have thought you'd have learned by now, Peter, that filthy little boys like you don't get happy endings.”

* * *

Peter turned 18 less than a week before graduation, and I marked the occasion by giving him 18 sturdy blows with a paddle and then tying him to my kitchen table and dripping birthday candles onto his body. He bore the pain to his torso with only the slightest gasps, until I let the hot wax run over his cock and balls, which caused him to mewl rather pitifully.

I told him he should be happy that I had shorn off his sparse pubic hair for the occasion, but as ever, he was not grateful for the tiny crumbs of generosity I threw his way.   
  
As I watched the wax dry on his smooth skin, as I peeled it off and marveled at the red streaks the wax left behind, I wondered why I had not thought to shave him earlier in our time together, for the sight of him, naked of even this last defense, was intensely arousing and made him look even younger than usual. For the first time, I considered that our time together did not have to end just because he had achieved the age of maturity, for even though my prurient interests tended to lay with adolescent males, Peter was the very definition of 'late bloomer,' and I could have happily enjoyed many more years in his company.   
  
Alas, the terms of our agreement were to cease upon his graduation, and though I acknowledge readily my vice and wickedness, at least in these private papers, I was not one to go back on my word.   
  
"Did you remember to make a wish?" I asked him as his belly drew taut from a fresh onslaught of the hot wax, and the hateful look he chanced to throw at me made me laugh.   
  
"How many shooting stars and lost eyelashes have you wasted wishing for my demise these past months?"   
  
"All of them," he muttered, and then cried out as I turned the steady molten drips into a stream.

Our last night together, Peter lay stretched on the hard surface of the desk in my home office, masturbating, while I glanced over the notes for my speech one last time. He had been told that he would climax no fewer than five times this evening, for I had determined that if I had to send him away from the shelter of my embrace, I would first ensure that his body was wrung dry.

His hand moved slowly along his shaft, and I paused in my revising to give him a penetrating look.   
  
"By all means, take your time Peter. We have all night."   
  
"What? But my roommate's expecting--"   
  
"Mr. Ionello is expecting nothing, for he is with the rest of your classmates, I'm sure, drinking himself silly at the old cemetery, as every graduating class has done for half a century."   
  
"But..."   
  
"Have you forgotten how to masturbate? How you used to beg me to let you touch yourself?"   
  
"No, Sir," he said sullenly.   
  
"Then close your eyes and think of your friend, I don't mind," I said, for my jealousy was eased by the knowledge that if Peter was moving out of my life, he was leaving Ned Leeds behind as well.   
  
Peter shook his head stubbornly.   
  
"No? Ahh, I see. You don't want to tarnish your friend’s image by bringing him into our games. I understand," I said, setting aside my notes. "Let me help you out."   
  
He shook his head, goose bumps breaking out over his naked flesh as I swept his hand aside, and I chuckled to think that my touch quite literally made his skin crawl.   
  
"Put your hands to your neck...no, like this," I said, and clipped his wrist manacles to his silver collar so that his fingers were laced behind his neck, his elbows pointing out to the sides. "Do not move your arms unless you want to choke yourself," I added.   
  
"No, please, I'll do it," he cried, but I ignored him. I continued to manipulate his cock while his breathing grew ragged, and finally he arched his back and ejaculated, his semen splashing over his taut belly and chest.   
  
"There's a boy, that's one."   
  
As he lay panting and trying to catch his breath, I opened my desk drawer and drew out a new toy I'd recently sent away for, a delightful dildo that concealed a set of batteries and vibrated when it was switched on. I teased his ass with it for several minutes, until he was hard again and low whines escaped his throat, and then I inserted the toy into his lubricated bottom and turned it on. He cried out from the overload of sensations, and soon he was climaxing again, his voice thready as he begged me for mercy.   
  
"That's two."   
  
I decided my work was finished for the evening, for really, it's the same speech every year, and I took him to my bedroom to enjoy his body one last night. I worked him over with the toy, my fingers, even my mouth at one point, when he swore it would be impossible to achieve another erection.    
  
“Nothing is impossible Peter,” I murmured, and was proven correct moments later when his soft and aching cock grew to fill my mouth.   
  
Through it all his body would squirm and writhe prettily, his unbound feet would scrabble against the bed covers when he grew overstimulated, and he would periodically forget his bound wrists and thrash until his airway was blocked. It was nearly midnight before I'd achieved the goal I'd set for us, and his final orgasm consisted of little more than a dribble of clear fluid.   
  
Then I fucked into his limp body until I was almost as exhausted as he was. We slept till dawn, when I awoke him to sink into his channel one last time.

* * *

The ceremony was to be held at noon in the auditorium, and was just as scintillating as any graduation ceremony, which is to say, not at all. The band played a mostly in-tune rendition of Elgar’s March, our top student gave a valedictory speech some variation of which I’d endured at dozens of graduations, and our little choir sang 'Graduation Day' while Prof. Quill looked on with misty eyes like the simpering fool he was.

When it was my turn to address the audience, I stared at Peter the whole time, and he met my gaze with a steely glare.   
  
"...And so I send the Class of 2020 off into the world knowing we at Midtown Preparatory have done everything possible to instill these fine young men with the discipline they need to achieve success, with the restraint they require to become valued contributing members of society, bound to this school in spirit even as they make their own paths in the world…."   
  
The crowd applauded politely. I winked at Peter.   
  
Then it was time to hand out diplomas. Prof. Rogers called each name as the students crossed the stage, pausing so I could shake their hands and we could pose together for the photographer.   
  
"Peter Parker."   
  
Peter walked across the stage, straight-backed and determined.   
  
"Congratulations, Mr. Parker," I said, crushing his hand in mine.   
  
"I still have friends here," he said softly, smiling for the camera. "And if you even think about taking on another 'intern,' I'll know."   
  
The camera flashed in our faces.   
  
"And what do you suppose you will do about it?"   
  
He adjusted his mortarboard to a cocky angle, still smiling.   
  
"What I should have done months ago, Headmaster. Cut your evil, vicious prick off."   
  
And then Prof. Rogers called the next name, and Peter Parker strode across the stage and out of my life.   
  
I shook hands with his aunt at the reception afterwards, told her what a marvelous job she'd done raising Peter without support, and the woman beamed.   
  
"It wasn't always easy, but he's a great kid. I’m so grateful for everything you've done for my boy."   
  
"It was my pleasure, Ms. Parker," I said with utmost sincerity.   
  
And then it was all over. Instructors took off for their vacations, cars were packed up with students' belongings, families drove away for a celebratory dinner before heading home, and I was left on campus alone.   
  
I walked to Peter's room in Danvers Hall that night, before the custodial staff could begin cleaning and airing out the dorms for the summer. I suppose I was feeling a bit melancholic, and wanted to take one last chance to breathe in Peter's scent. The room was completely empty save for a small pile of items on Peter's bed.   
  
He must have feigned forgetfulness and come back alone while his family waited in the car, I realized, for lying on the bed was his collar, twisted out of shape and mangled by the pair of bolt cutters lying next to it, as well as the wooden box I had given him months ago, now smashed to splinters. The plugs inside were largely unharmed, as they were made from one of those hardy silicone polymers, but everything else was broken beyond repair.   
  
I lay down on the bed and pressed my nose into the mattress, where I could just detect the lingering fragrance of Peter's musky teenage scent, and masturbated furiously, coming with a cry on the ruined collar.   
  
And that is where the story of my obsession with Peter Parker should have ended.

Several weeks later I was in my office sipping a cup of tea, in an unusually contemplative mood. I was sifting through another batch of mediocre faculty CVs, but my mind kept wandering. I found myself wondering if I should be pulling up stakes instead of preparing for the new school year. Now that I was no longer spending every waking moment tormenting the boy, I could see that my fixation with Peter had caused me to grow careless, behave recklessly, for I had been so bewitched by his lithe young body that it's a wonder I hadn't raised serious suspicion. As it was I had drawn the attention of that blasted Romanoff woman, and Elise had been giving me sideways glances on and off all spring. And Flash Thompson, I felt sure, suspected something strange in our relationship, for I now realized that nobody on campus but myself watched Peter with more interest.   
  
Yes, this year could have gone quite badly for me if we had been discovered, if just one adult had paid a little more attention to their students and a little less to their own pathetic lives.   
  
It might indeed be time to find a new job, a new hunting ground. I decided I would give it some serious thought when I returned from my jaunt to Tennessee, for my good friend Skip had sensed my dolorous mood and invited me to spend a few days with him and his pet Harley. I felt sure that a weekend of watching Skip exploit the boy's mind while we shared his body would cheer me up and clear my head.   
  
I pushed the applicant papers aside for the moment and picked up a copy of the Chronicle of Higher Education, just to see what might be out there for an administrator with my credentials. Maybe college boys would not be quite so tempting to me; maybe it was time to start dating lonely widows again. Maybe I could actually write that educational manual everybody thought I had spent the year writing, while I had been instead playing out my most wicked and deviant fantasies on the canvas of Peter's milk-pale skin.   
  
I wondered where Peter was now, if he was recovering from our time together in his aunt's house or if he had already set off for a bright future at MIT. Was he living in the dormitories, or had he secured his own lodgings? I longed to join him in Massachusetts, for I had many more things to teach him and so much to show him of the world’s darkest secrets. Private clubs where I could display Peter, where he could finally be presented as mine, all eyes on him as I flogged him and wrested orgasms from his resisting body before an adoring crowd. Clubs that maintained devices I had not the space for in my modest home, such as stocks and wooden crosses and pulleys that could be used to suspend his naked body. Shops where I could readily procure new toys to torture him with, such as a plastic chastity cage I had seen advertised in the back pages of a pornographic magazine, not so pretty as the cage he had destroyed but safer for long-term use, and more discreet when worn under his clothes.   
  
I sipped my tea and turned to the Career Opportunities section of the paper, and my eyes were drawn immediately to one specific advertisement.    
  
My body hummed and my blood sang; my cock fattened in my trousers. For I had promised Peter his freedom when he graduated, but I realized as I read and re-read the ad that I had not specified from which institution this graduation must occur. I turned to my reference shelf, where I kept a directory of college and university personnel, and picked up my phone.   
  
"Is this the line for MIT? Ah, President. This is the Headmaster at Midtown Preparatory in New York. I'm not sure if you remember me, but we met at a fundraiser in Chicago last year. We discussed Stark Industries recent donations to your students projects. Indeed? Lovely. Well, I just happened across an advertisement in the Chronicle for a Dean of Students at your school, and I wonder if you have time to tell me a bit about the position?"

**Notes for the Chapter:**

> I hope you enjoyed this story. The Headmaster is absolutely terrible which means he's a pleasure to write. The devils were inside us the entire time, after all. Again, I hope you enjoyed. Please leave a comment with your thoughts if you did.

**Author's Note:**

> Leave a comment if you enjoyed :)


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